Subject Index 1972

Subject Index 1972 ACeneS detritiation, 2191 Acetala silylated ketene - , thermal condensation with aldehydes, 79 Acid Chloridea ketone synthesis with Grignard reagents, 467 unsaturated; 1253 Acids abscisic - , sesquiterpene CD, 2521 o-amino - ,314s stereospecific synthesis, 2565, 2-aminofruns-2-decalin-carboxylic - ,4157

asparagusic - , 2549 o-bromo - ,4067 carboxylic - , cathodic synthesis, 4809 enantiomeric, absolute confii., 3873 esterification, 757 hindered, esteritication, 4063 homopiperonylic and homoveratric -, 1383 hydrocimramic - ,4823 a-hydroxy - ,485s hydroxy fatty - , 1127 n- dicarbonic - , Lewis - , reaction with N-chloramines, 993 metalated carboxylic - , 79 3-methoxy-homophthalic acid, 1615 nitrous - , with erythromycin hydrazone, 29 phenylacetic - , new synthesis, 1381 prostanoic - , Nef reaction, 3815

Acids (continued) Adamantanes (continued) N-acetyl-(l-adamantyl) amide, 2_(Cpyridyl) alkanoid - , 1237 1253 salicylic, electrochemical reduction, photoelectron spectra, 5285 3433 polyhaloadamantanes, 3191 -‘--oidal, 1515 lO-protoadamantyl cations, 699 7-syn-6vndodihydroxybicyclo spiro [adamantane-2,2’-adaman12.2.11 heutane 2-endo-carboxvtanel. 1175.1179 Uc acid-o&tone. 35 1 _ Addition r&ctiona tartaric - , derivs, 5227 2-alkyl propenes to disiamyl tenuazonic - , phytotoxic extracts, borane, steric effects, 245 13 allylic and homoallylic double tri-t-butyl-cyclobutene dicarboxybond participation, 509 lit acid, electrolysis, 4483 amido radical to alkenes, 535 viridomimc acids A and B, chlorosis dewar benzene and dewar beninducing fungus metabolites, zene diol, 3 129 3789 diazomethane to aromatic sulviridominic - , steroidal metaphines, 2293 bolite, 199 dimethylketene to 1, Zcyclonoweak, ion pair extraction, 473 nadiene, 1189 A&dines dimethylketene to 1, 3-dimethyl2, 7-dimethylacridine lO-oxide, allene, 2499 photolysis, 971,977 diphenylcyclobutenedione with 1,2, 3,4,5,6, 7, I-octahydro - , methyl phosphite, 787 929 electrophilic, to semibulhalene, Acylation 383 nucleophilic, carbohydrates, 3945 N-cholrosulphonly isocyanate to diphenylmethylenecycloAcyf group migration, steroid acetates, 3349 propane, 1551,390l unsaturated acyl chlorides, intranitro compds. to ynamines, 41 molicular cyclization, 749 O-arylhydroxylamines to diAdamantarms methyl acetylenedicarboadamantene, 4049 xylate, 3941 adamantylideneadamantane peroxprostaglandin synthesis, 2627 ide, 169 transannular, heteroadaman2-alkyl-2-adamantanols, NMR, tanes, 801 4103 unsaturated organometallics to I,3-bishomoadamantane, 4887 methoxy and carbonyl groups, hetero - , 801 37

...

Subject Index Alkenes (continued) new synthesis via p-hydroxy sulphoxides, 649 nitro - , photorearrangement, 2861 NMR, 14.5 noncoplanar double bonds, reactivity, 475 openchain - , polar addition, 2895 oxidation, improved, KMnO,, 4901 with thallium triacetate, 347 1-phenylcyclohexene, photolysis, 2663 2-phenyl-2-oxazol-one cycloaddition, 4039 photocycloaddition to O-alkyl thiobenzoates, 4993 propylenebutadiene codimerization, 4175 strained, ‘%TNMR, 4821 styrene and stilbene with dibenzoylfuroxan, 3469 synthesis, unsymmetrical, 407 via @hydroxylalkyl phenyl sulphides, 737 with iron pentacarbonyl, 4435 terminal, oxygenation to ketones, 5273 triethylorthoformate addition, 1291 AlkOXidt?S

diaryliodonium - , decomp., 3301 dichloromethyl - , a-metalation, 4117 sodium - , with diarylbromonium salts, 4817 ARo=Y BroUP addition to organometallics, 37 methoxyl group migration, 4407 Alkylation active methylene compounds, 1279 ambident anions, pressure effects, 493 4- bromocrotonate, 1507 carboxylate salts, 4063 chloroformate esters, new, 3921 cyanomethycopper, unsaturated nitrile synthesis, 487 2,7_dimethylacridine lO-oxide, photolysis, 971, 977 dimethylphosphono- and diphenylphosphinyldiazomethane, 3979 electrophilic, by enamines, 3799 enolate, 4903 methylene group of diphenylmethane, 691 A”9-2-octalones, 3305 resorcinols, 945 thioketals, 1085

Ill

Allrylotion (continued) transalkylation of aromatic hydra carbons, 3687 weak acids, ion-pair extraction, 473 Aurynes acetylenic halides, electroreductive cyclization, 453 diethylaminopropyne with pyridazines, 1517 aryl - , synthesis from arylcopper compounds, 5209 cationoid electrophiles in nitroalkanes, 4935 5-chloro3enel-ynes with enamines, 4545 cycloaddition to thiophenes, 5269 cyclopropenium ions giving - , 3765 a-diazo ketones, 4533 dicyanoacetylene, Diels-Alder reaction with thiophene, 605 dimethyl acetylenedicarboxylate, addition to O-arylhydroxylamines, 3941 diphenylacetylene addition to carbonium ions giving indenes, 2869 formyl-ethynyl conversion, 3769 haloacetylenes, NMR, 4023 heterocyclic - , oxidative coupling, 4831 hydroformylation, 3455 isoquinolinium ylids, 3325 4-methyl-hexa-1,2diene5-yne, Cope rearrangement, 3571 N, N-dimethylpropargylamine, proton transfer, 521 phenylacetylene with dibenzylfuroxan, 3469 photochemistry, with metal carbonyls, 1589 trimerization of conjugated - , selective catalysis, 6 1 vi&tat diacetylenes with 0,. 1035 ynediamines, 85 Aflenes diastereomeric monocylcic di - , 3425 dichloroketene adducts, NMR, 1245 1, 3-dimethyl - , addn, to dimethyl ketene, 2499 S-(+)-l, 3-dipheny1aIlene and triphenylallene, dimerization, 1265 fulvenallene, 3917 synthesis, 1249 hydrogenation, selective, 1391 viny1 allenyl magnesium, 4465 Auyl Broup allylic acetates, Zn/HCl reduction, 725 allylic Grignard addn. to C = C, 2285

AIIyl group (continued) allylic halides, unsaturated nitriles from, 487 a-ally1 ketones, esters and nitriles, 3257 allylfithium reagents, allylic cross coupling reaction, 1471 n-allylnickel intermediates in alkene synthesis, 1433 ethers, with allyllithium, 2411 methanallyl fragment, 4627 o-methylmuconateq functionalization, 407 1 Aluminium compound8 trimethylaluminium with glycidic esters, 1001 Amides acetamide-phenol interaction, IR, 4457 acetanilides, hydrolysis, 5 24 1 amido radicals, hindered rotation, 1413 aminoalkyl malonic ester - , 15 19 l-benzyl-I, 4_dihydronicotinamide, dimerization, 4883 cY_chloro-o,o-diphenylacetamide with potassium phenylcyanide, 805 diastereoisomeric secondary, 3873 dimethylformamide, peroxyester reaction, 4395 N, N, N’-trimethylbenzamide with phenylisothiocyanates. 4699 protonation, 2485 vinvloa acid - . 2607

Anlaika-

hindered rotation, 5281 Amination N-and S-, 4133,4137 Amine oxides aromatic - , electrochemical oxidation, 427 pyridine N-oxide, Grignard reaction, 3 11 Amines acyclic trialkyl - , pyramidality and rotational barriers, 129 aminated 1, Cbenzoquinone, photochem., 2253 o-aminoacids, 3 145 stereospecific synthesis, 2565 aminocyclobutyl methyl ketones, 4663 a-aminoethers, epimerization, 3773 amino pyridines, ionization potentials, 3 193 anopterine, alkaloid, 2727 benzylamine and p-aminotoluene, mass spectra, 1109 butadiene and l&and effects of catalyst, 2773 I-chloro-2-methyl-azindines and azetidine, 1301

Tetrahedron Letters 1972

iv Amine4 (continued) diethanolamine, with fhroraolkenes, 3957 diethylamine with butadiene, 4197 enantiomeric, absolute config, 3873 guanidine with benzaldehyde, 3983 heteronuclear bicyclic - , NMR shift reagent, 2631 hindered - . ouatemization. 3857 morpholine’s&hesis, aminbmercuration, 4013 N-bromo - , solvolysis, 875 NMR shift reagent complexes, 435 N, Ndialkyl (octa-cis-2,6-dienyl) amine, 4009 N, Ndimethylpropargylamine, proton transfer, 521 o-substituted benzylamines, isoquinolines from, 3149 primary, acetoxime with organomagnesium 1007 with lithium reagents, 2811 secondary, aliphatic - , with benzofuroxans, 5365 from primary, 2807 with 2,4-dimethoxy pyrylium salts, 217 silylation, 525 vinyl - , enamine equilibria, 2837 NMR, 4443 AlllhOddS

cysteine ethyl ester with p-benzoquinone, 1327 ketimine derivs, peptide synthesis, 2261 oligo-L-prolline, 3795 svnthesis from nitriles. 1199 synthetic peptide amides, 101 tyrosine, 0-benzyl protection, 3475 ynediamines, 85 Aminogzoup ESR of oxidation products, 4751 Ammonium aalta l-arylethylammonium ions with sodium ethoxide. E2.9 17 pentacyanines with cyclopentadienide, 1021 AllChhariC

glycol monobenzbate hydrolysis, 4617 AnhydrideS benzoic dithiocarbamic anhydride, 4785 bis_2,3diphenylcyclopropene anhydrides, 1579 carboxyliocarbamic - ,439s 2-carboxymethyl-3-N-hexyl-maleic acid - , metaboltte, 3519 homophthalic - , pyrolysis, 1249

Anhydrides (continued) sulphenocarboxylic acid anhydride deriv. of 1, 2-oxathioleS-one, 3689 AliOnS

ambident, alkylation, effect of pressure, 493 aromatic radical - , reduction, 2495 aziridinyl C - 13591 AnneBation nonafulvalenes, 721 AmIulenea [ 131 annulenone, perturbed, model compound, 331 [ 151 anntilenone, perturbed, 3389 benz-annelated bridged hetero [11],4129 4: 7,10:13-dioxide [15]annulenone system, diamagnetic shifts, 153 1, 14di-t-butyl-5, lO-diphenyl-6, 8,15,17-tetrahydro [ 181 - , 3253 heterocirculenes, 763 macrocyclic dehydroannulenones, 3691.3695 1,6-methano [lo] annulen-llones, 2223 1,6-methanocyclodecapentaene, 4107 symmetry-forbidden reactions, 3, 9, 12, 18-tetra-t-butyl- and 3, 12-di-t-butyl-9, 18-diphenyl-1, lodidehydro [ 181 - ,316l 3, 13, 16,26-tetra-t-butyl-1, 14 didehydro [ 261 annulene, 4253 3, 7, 10, 14-tetrasubstituted, I, 8 didehydro [ 141 - ,3157 Anodic reactions coupling of aryl ethers, 227 1 1, 2dithiol-3-thiones, oxidation, 771 oxidation, restrained, 965 trifhroroacetoxyration of methylbenzenes, 47 1 AnthCeneS

anodic oxidation, 1449 3,4-dihydro-1,9, 10 (2H) anthracenetrione, dimerization, 73 1 (-) flavoskyrin, 735 AnthraquinoneS aniofuranoside - .5013 Antibacterial agents ’ 3-methylenecepham derivs, 3241, 3245 quinone hydroquinone pair, 795 Antibiotics ascufuranone, 2541 aureotine, 4875 C-nucleoside, 3945 deacetylcephalosporin, converion, 1585

Antibiotics (continued) 1,4dimethoxy-2-nitro-3,5,6trichlorobenzene, 2 1 I 6-epi-penicillins, 285 erythromycylamine, new route, 29 ikarugamycin, stereochem., 2557 structure, 1181, 1185 polyene, cyclic hemiketal structures, 5053 pyrazomycin, nucleoside, 2279 1,2-secopenicillin, 4387 terpenoid, LL Z1271a, synthesis, 695 uhginosin B, 4787 Arenes substituted, chemical shifts of non-aromatic protons, 681 Aromatic compounds biphenyl, unsymmetric, 4985 8-chlorohomotropylium salts and 7, 8-dichlorocycloocta-1, 3, 5triene, 3661,3665 isodurene, orientation of chlorination, 4 16 1 non-benzenoid, 4859 [14] annulens, 3157,316l nonppyridinoid aza - ,3273 phenol from, lead tetrakistrifluoroacetate, 5369 hmaticity anti - . cyclobutadiene. 1025 cyciopentadienone, 4n system, semibullvalene, 383 anti-aromatic heterocycles, 953 cyclobutadiene, anti - , 5 113 definition, harmonic oscillator model, 3839 delocalization energy, redox systems, 4835 4:7, 10:13-dioxido[l5]annult+ none system, diamagnetic shifts, 153 hetero - , N-vinyliminopyridinium ylides, 5245 heterocirculenes, 763 hexamethyl Dewarbenzene, 4733 1,6-methano-cyclodecapentaene, 4107 o-xylylene, cycloaddition, 2443 phospholes, NMR, 3353 pseudo - , enamino ketone photothem., 2513 resonance energies from equilib rium data, 5019 tetrahydrol181 annulene, 3253

Aromatizition . cvcloalkenes with TFA. 903 dðyCDewar benzenes, 3509 steroidal enediols and triols, 4501 Arsenic compounds arsabarrelene and arsabenzene,3961

V

Subject Index

AwnmeW diastereomeric monocyclic diallenes, 3425 induction, t-butyl bonded to carbonyl, 5289,5293 nonracemic helicenes, 2 195 optically active alcohols, 4605 synthesis on insoluble polymer support, 4855 Autoxidation ketene, 3397 Aza compounds azabicyclononatrieneq 4569 2-azabicyclo[ 3.3.11 non-lene systems, 335 aza-cannabinols, 545 2-azasteroids. 3237 azasulphonium salts, 497 cyano 2-azapropenoid, 4771 polyaza-macrobicyclic compds, 4557 tetraazapyrene and N-oxides, 3643 Azepines 1, 2-di - , anion, 4891 dihydrobenz - ,332l (l-H)-1,2-diazepines, 3575 2-phenyl-benzazepine alkaloids, 4431 Azetidines azetidm-3-one, synthesis and reactions, 5063 azetidinones, optically active, 2793 2-azetidinones, from penicillins, 5097 I-chloro-2-methyl - , config. and octant ru?e,. 1301 4-phenylazetrdm-2-one and 4methy&phenylazetidm-2one, 2789 Azides exo-7-azidobicyclo[4.1.0] heptane, 3933 singlet oxygen reactions, role, 49 toluenepsulphonyl - , with 2carbethoxy-l-methylindole, 3949 tri-t-butylcyclopropenyl - , 3293 &sines azolo - ,4179 heterocyclic aromatic bis - ,629 isomeric dihydro - , NhfR, 1417 oxidation of ammonia, 635 Aziridinea aziridinium ylids, fragmentation, 3827,4659 l-chloro-2-methyl - , config. and octant rule, 1301 cleavage, cf epoxide, 2591 2, 2-dichloro3-p-nitrophenyl-lphenyl

- ,359l

l- hydroxyaziridines,

3995

Ahidineu (continued) N-cyanoaziridines,ring opening, 4121 Azirmea aryl - , photocycloaddition to hetero multiple bonds, 4087 1-azirines. cycloaddition to ketenes, 1353. -

Azochm

l-alkyl-1,6-dihydro-l-benzazCb tine, 4863 AZ0 compound9 azobenzene, photochem. dehydrogenation, 2493 cyclic - , compds., 1225 decomposition rates, 339 diethyl azodicarboxylate, 1279 dehydration agent, pnitrophenylazotriphenylmethane, 1221 thermolysis, 387 rrans-azo linkages in cyclic compds., 4565 Azulenes hydro - ,4973

arsa-93961 dihydro - ,175 Bases ambident, pmethylanisole, 1477 base ion-pairing in bimolecular eliminations, 7 11 bimolecular elimination, base ionpairing, 265 promoted p-eliminations from rrans-2-phenylcyclopentyl tosylate, 3819 thymine : 3,4-benzopyrine photoproduct, 589 Basic&y ferrocene and related compds, 269 phenylpyridines and thienylpyridines, 233 Benzene afky -3 complex layer with aluminium chloride and hydrogen chloride, 5259 endo addition to Dewarbenzene, 3129 fluoro - , nucleophilic photosubstitution, 685 hexamethylDe&r -, 5357,536l methylbenzenes, anodic trifluoroacetoxylation, 47 1 orrho-substituents, reactivity, 3203 semibenzene formation, 1019 Benzoylation reagent for, benzoic dithiocarbamic anhydride, 4785

Benzyne benzocyclobutenedione photolysis, 5321 cr-diazo ketones and, 4533 insertion reaction with alkylbenzenes, 4141 Betainea bicyclic. ring opening, 3965 ‘I-norbomanylidene and ‘I-norbomenylidene, olefinic capture, 5 117 strained cyclic - ,2603 sulphonium - , decomp. to epoxides, 33 13 2-troponyethoxycarbonylmethylenetriphenylphosphonium betaine, X-ray, 1611 BicycRc compounds allene, strained, 287 1 2-aminotrans-2-decalin-carboxylic acids, 4157 aza - , N-chloramines with Lewis acids, 993 solvolysis of N-bromaomines, 875 7-azabicycloheptyl-N-oxyl derivs, 3317 azabicyclononatrienes, 4569 2-azabicyclo[ 3.3.11 non-l-ene systems, 335 azabicyclo[3.2.1]system, 531 2-aza-foxobicyclo[ 2.2.01 hex5ene, 3563 2, 3-benzobicyclo [ 3.2.01 hepta2,6-dienes, 2, 3-benzobicyclo [4.1.0] hepta-2,4-dienes benzo[b]-1,4-diazobicyclo[3.2.1] octane, NMR (shift reagent), 2631 bibenzobicyclo [4.2.1] nonodienes, 3747 bicycle [4.2.2] deca-2,4,7,9tetraene, 2677 bicycle (4.2.21 deca-2,4,9-trien7-one, 2677 bicycle [ 3.1.1) heptanone, 4573 bicycle [ 4.1 .O] heptanone, 3625 bicycle [ 2.2.11 heptene ring formation, 3401 bicycle [ 3.1 .O] hex-Zen-endedcarboxaldehydes, sigmatropic hydrogen shifts, 125 bicycle [ 3.1 .O) hexenone-2, C cyclohexadienone, 2735 bicycle [ 2.2.21 octadienes, 4511 bicycle [ 2.2.21 octene derivs., ketene equivalents evaluation, 121 bicycle [ 3.3.01 octyl system, 383 bicyclopentane isomerization, 3713 bridged, conformation of ring enlargement, 4867

vi Bicydic compounds (continued) 4-bromobicyclo[3.2.0]-hept-2-ene. base catalysed elimination, 3531 camphor, Schmidt reaction, 187 camphor sulphonamides, 985 &chloro- and fi-tosylketals, fragmentation, 5225 &decal&2,6-dione synthesis, 137 1,5-diazabicyclo[4.3.0] non+ene, 3987 3-diaxo-2-norbomanones, decomposition, 1069,1073 7,7-dibromobicyclo[4.1.0] heptane, solvolysis, 4427 7,7-dibromobicyclo[4.1.0] hept3-ene with methyl lithium, 539 1, 2-dimethyl-2-norbornyl cations, 2447 exe-7-azidobicyclo[4.1.0] heptane, decomp., 3933 exo/endo-S-methoxy-bicyclo[ 2.1. [2.1.0] pentane, isomerization, 359 exo/endo+substituted bicyclo[ 2.1.01 pentanes, synthesis and reactivity, 363 exo-bicyclo[ 2.1.0) pentyl tosylate, solvolysis, 359 exo-norbicycloekasantalal, 2207 exoJ-substituted bicyclo[2.1.0]pentanes, 355 1 hexo-pyranoside derivs., ‘% NMR, 4879 iodolactones of bicyclo[ 2.2.1]heptanes, with hydroxide ion. 1143 methyl-[ 3.2.01 bicyclohept-Zen7-ones. thermolvsis. 5.191 5-methylene-bicycl& 212.1) heptZene, 3465 norbornadiene, hydrogenation, 2503 norbomenyl system, neighbouring group participation, 347 A”9-2-octalones, reductive alkyation, 3305 3-oxotropanium salts, equilibration, 1525 (+)_2,2,4,4,6-pentamethyl-3azabicyclo(3.3.11 nonan-F one-3-oxyl,4287 perchloro4-methylen~bicyclo[3.2.0] hepta-2,6-diene, 2613 phenol-dienone isomeriaation, 1341 polyaza-macrobicyclic compds, 4557 rigid, NMR study, 3277 Spiro-norcaradiene, 1255, 1259 u-substituted nitroso compd., rearrangement, 7

Tetrahedron Letters 1972 Bicyclic compounds (continued) 7-substituted norcaradienes, 345 1 7-synd-endo-dihydroxybicyclo[2.2.1] heptane 2_endo-carboxylic acid-o-lactone, 35 1 BiO@l&? cedrene, sesquiterpene, 2455 skimmianine, 2199 Biologically active compounds boll weevil sex attractants, 669 cannobinoids, analogues, 545 synthesis, 945 detoxin D, ,2509 leptostachyol acetate, insecticidal lignan, 653 lunularic acid, growth inhibitor, 1615 penicillins and cephalosporins, antibacterials and antimicrobials, 375 phytotoxic compds. from pyriculavia oryzae Cavara, 13 tetracyclic diterpenes from rho dodendron, 1381 tetracyclic gibberellin, 3 115 tetrahydrocannabinols, 2507 Bioluminescence 2-aminopyrazine, aequorea jellyfish, 2747 Biosynthesis aureothin, nitro metabolite, 2701 gibberellin, 4299 2kitogLutarate, 4685 L-leucine incorporation into indolealkaloids. 2659 monoterpenks, head to tail, 67,71 Bond carbon-nitrogen, high rotation barriers, 5239 cyclobutyl bonding electrons, participation, 387 internucleotidic, 3437 polarization, trans-l-subs-l, 3butadienes, 3329 torsion round S&N, 505 1 Boron compounds 3-alkyl-trans-1, 2-diols from Q, & unsat. ketones, 4031 I, 2+yclotridecadiene, dihydroboration, 4871 diborane, improved prep., 3173 organ0 - , bialkyls and biaryls, 2193 trialkyl boranes, ring expansion of unsaturated cyclopropanes by, 1605 with p-dicarbonyls, photothem., 1167 Bridged compounds 2-aminomethylnorbornan-2-ols, deamination, 4867 azoloazines, 4179 berm-annelated hetero [ 111 annulenes, 4129

Bridged compounds (continued) bridgehead enolisation, ent-17norkauran-16-one, 4 111 t-endo-hydroxymethyl-5-norbornene, NMR shift reagent, 5039 7-methyl-7-norbornyl tosylate, solvolysis in fluoroalcohols, 3617 nitrogen heterocycles via imide reduction, 4493 norbornadiene with benzophenone triplets, 5345 norbornan-2-one, stereochem. of ring enlargement, 4867 norbornene, thiol addn., 2719 7-oxanorbornadienes, isomerization, 496 1 polycyclics, with diiron nonacarbonyl, 5325 pol;~2~oalkanes. conformation, Bromination alkenes, nucleophilic participation of HMPT, 1209 5.6-dimethoxvuhthalide. 1197 h&tones, 2489photo - , bridged, bromoalkyl radicals, 3 17 pyrimidine, gas phase, 2 183 Bromine compounds 4-bromocrotonates,7-alkylation, 1507 ol-bromoesters and o-bromoacids, 4067

bromohydrin formation in DMSO, 1057 13-bromo[ 71 metacyclophane, 403 diarylbromonium salts with sodium alkoxides, 48 17 1, 1-dibromoalkenes, conversion to alkynes, 3769 7, 7-dibromobicyclo [ 4.1 .O] heptane, solvolysis, 4427 o, a’-dibromoketones, electrochemical reduction, 4079 laurefucin, alcohol from laurencia nipponica 3 N-bromoamines, solvolysis, 875 t-Butvl zrouu bonied tb carbonyl, asymmetric induction. 5289.5293 t-butylation of 2-naphthol, 4183 3-t-butylcyclohexene, electrophilic attack, 3527 ethylenic phosphines, influence, 145

Cage structuree homocubyl derivs, 4541 pentacyclo[6.5.0.0”V4 .O’~‘.O”““] trideca-5, 11-diene, 4537

Subject Index Calcium electrically neutral carrier for Ca” , 2473 Carbamates N-(dimethoxvnhosuhinothioyl) ‘carbamate esters, 4245 Carbanions acyclic a-sulphinyl - , relative stabilities, 4839 nitrostabilized - . 35 1 I Carbenes 2-, 3- and 4-pyridyl - , isomerization, 2239 anthronylidene, addition to alkenes, 3491 carbenoid centres, methoxyl migration, 4407 carbenoid rearrangement, 4117 dichloro - , 1461 meso-tetraphenylporphine addition, 1011 phenalenylidene, 2749 phenylthio - , 3587 Carbohydrates aldehydo 2, 3-dideoxyhex-2-enose triacetate, oxidation, 3 15 1 bicyclic hexo-pyranoside derivs., ‘% NMR, 4879 branched chain sugars, 5353 diamino-didesoxy-hexoses, 346 I di and polyaminosugars, 3461 D-glucose, conversion to 2-(hydroxyacetyl)-furan, 48 13 gibberellm-A, -0(3)-p-D-glucopyranoside, 4053 mass spectra, MW determinations, 4827 nucleophilic acylation, 3945 oligosaccharides, solid phase synthesis, 5065 oxidation, ferrate (VI) ion, 4143 synthesis from telomers of vinylene carbonate, 2219 uloses with or-metalated isocyanoacetic esters, 5353 Carbonates Bayer-Villiger oxidation, 5081 vinylene - , synthesis of sugar derivs., 2219 Carboulum ions dehydration of alcohols in HMPA, 165 indenes from, 2869 a-keto - ,256l new stable type, 4851 trapping by thiophenoxide and borohydride, 895 Carbonylation organometallic, 2803 Carbonyl compounds alkyne hydroformylation, 3455 aromatic - , with trimethylchIorosilanc/magnesium, 75

Vii

Cations (continued) Carbonyl compounds (conGnu&) 7-cycloheptadienyl cations, 4403 azines from, by ammonia oxip-cyclopropylethyl - , 3249 dation, 635 1, 2-dimethyl-2-norbornyl - , azodi - , addn. to alkenes, 47 13 2447 carbonyl-donor partial chargeelectrophiles with alkynes, 4935 transfer interactions, 2163 1-methoxyhomotropylium ion, conversion to gem-dimethyl, 293 4399 diiron nonacarbonyl with bridged trishomocyclopropenyl- ,4 17 I polycyclics, 5325 tropolonyl-5-cyclopropenium - , p-di - , photochem with trialkyl2227 boranes, 1167 uracil dication, 3823 nickel titracarbonyl reduction, ceuhalosRorins 2219 -C,-alkoxy, 3717 photochemical 1, 3-cycloaddition 6- and ‘I-alkvl - .49 17 to oxiranes, 5 133 desacetoxy 1 , synthesis, 5097 transition metal carbonyls, 3 183 7-phthalimido-8-t-butoxyd, 8Carbonyl group seco-desacetylcephalosporanic addition to organometallics, steric aced lactone, 5301 course, 37 conjugation with cyclopropane, Ch&OneS cryptocaryone, novel 5’,6’-di997 hydro -, 3419 Carboxylation acyclic 4-enones, and 4, 5-dihydroCh=Se carbonyl-donor partial charge pyrans, 4707 transfer interactions, 2163 electro - ,4809 density, organo-metal sulphides, Carcinogens 5341 thymine : 3,4-benzopyrine phototransfer complexes, 2639 product, 589 fluorescence, 3363 Carotenoids 7-cis-p-ionol, ring chain conformers, Chemiluminescence twistanes, failure of octant rule, NMR, 3915 4275 photo-oxygenation, 25 17 Catalysis Chirality asymmetric solvent catalysis, alkene formation with allylnickel organo-cadmium compds., complexes, 1433 5227 aromatic hydrocarbon transalkytwistane, 4355 lation, 3687 Chloramines butadiene-amine reaction, ligand reaction with Lewis acids, 993 effects, 2113 Chlorination chlorotris (triphenylphosphine) epoxides by triphenylphosphiue rhodium allene hydrogenation, in Ccl,, 3869 1391 isodurene, orientation, 4161 dimethyl diazomalonate, active specific, Nchloropolymaleimide, copper catalysed decomp., 5173 3903 Chlorine compounds hydrogen transfer, 10 15 chloranil, photochem, 3 125 linear octadiene formation. 163 8-chloroadenosine, 2595 metal, cyclopropene ring opening, chloroformate esters, 957 3367 . choromethyl cyclohexenes, 1091 micelle, pnitrophenyl acetate %I incorporation, 807,811,817 hydrolysis, 458 1 phase transfer - , mechanism DDT, dehydrochlorination, 2887, 2891 4521 selective, trimerisation of con3,4-dichlorocycloheptatriene, jugated acetylenes, 6 1 5235 dichloromethyl-alkoxides, asilver ion, elemol to eudesmols, 5 I39 metalation, 4117 zeolites, cyclopropene dimerization to tricyclohexanes, 23 1 hexachloracyclohexanes, isomerization, 4807 cations hindered chlorophenols, antiallylic - , 1057 oxidant properties, 3743 6, 7-benzo-4,9-oxide [ 1 I ] annulenvl - _4129 linarioside, iridoid glucoside, 419 2- but;1 - ,‘hydrogen bridging, 1241

...

WI

Tetrahedron Letters 1972

Chlorine compounds (conlhued) linarioside, iridoid glucoside, 419 monodechloraoldrin and monodechloroisodrin, rearrangs ments, 13 11 pentachlorobenzonitrile, 4169 truns- 1, 4-dichlorocyclohexane, 4965 ChlOlMll8

chromanone imine self condensation, 1445 6,7-dimethoxychroman4one, 1445 3-prenyl - , 3371 Chromened 4, Cdimethyl - ,4453 Chromones nuclear C-methylated, 1 I01 pyrazolo - , 1593 Chromophores phosgene with 4-(4’-nitrobenzyl) pyridine, 27 circular dichroism abscisic acid, sesquiterpene, 25 2 1 calamenes, sesquiterpenes, 905 iboga and voacanga alkaloids, 2763 ketones, front octant effects, 13 15 linear nonplanar polyenes, 597 6-methylspiro[4.4] nonan-l-one, 883 nitrosamine acids, 779 steroidal enone photochemistry, 1061 thioloy-&tones, 3 165 Cleavage reactions aziridines and epoxides, 2591 cyclopropane ring - , by photooxidation, 9 cyclopropenones, 4415.4419 O- alkyl, methyl esters, 3987 S-&steroids, ring A - , 261 thioketals, 1085 Complexes alkylcopper(1) with carbon monoxide, ketone synthesis, 2803 allylnickel, 1433 aluminium alkyl-sparteine - , methyl crotonate dimerization, 4477 benzylidene anilines with Pd(ll), Pt(l1) and Rh(II) chlorides, 459 charge transfer, fluorescence, 3363 cyclanone-TiCl,, IR, 4563 @-kitosulphonium halides with copper halides, reaction with ethyl diazoacetate, 407 ligand-curopium, 3539 metal-nitrene, 1065 metal, with tetrapyrrole ligands, 3803 neutral carrier for Ca+’ , 2473 rhodium porphyrin, 1077

Coudensatlon reactions aldol, structure influence, 5085 enolate ylids with ketones, 933 Grignard reagents with acid chlorides giving ketones, 467 intramolecular. aldol -. of imidoester, 5109’ ’ N-(2_cyanomethyItryptophyl) pyridinium tosylates,_ _ 2639 phenyhnalodinitrile with diphenylcyclopropenone, 3883 thermal - , sllylated ketene acetals with aromatic aldehydes, Confiition absolute, farfugin A, 5 25 1 santolina alchohol, 7 1 2-amino-rrans-2-decalin-carboxytic acids, 4 157 axivalin, sesquiterpene lactone, 4423 camphor sulphonamides, 985 cytosine nucleosides, 3991 determination by X-ray anomalous scattering, 1323 helicene and heterohelicenes, 2839 iboga and voacanga alkaloids, chiroptical approach, 2763 inversion, fused cylcopropane ring opening, 22 1 loliolide and dihydroactinidiolide, 2517 oxiranyl radical, 981 oxymercurials by NMR, 4327 4-phenylazetidin-2-one and 4methyWphenylazetidin-2-one, 2789 phosphaporphyrins, 1111,1115 quaternary centres with C-l, 3 dithianyl branched chains, 5163 S-methyl thioimidates, 2655 p-substituted enamines, 3603 toxol, (-)-2-iso-propenyl-3-hydroxy-5-acetyl-2, 3-dihydrobenzofuran, 2873 Conformation 1- and 4-chlorodiamantane, 1547 benzene rings in cyclophanes, 4981 carbon-phosphorous bond rotation, 3261 cyclic dipeptides, 483 cyclic thisulphinates, 203 1,2_disubstituted chlormethyl cyclohexenes, 109 1 ethoxyethene, 2243 halogenocyclohexanones and halogenodecalones, 277 halogen with alkyl radicals, 2427 N-alkyl groups in N, N’-diisopropyl thioacetamide, 3843 N-aralkyl-pyridinium ions, 3429 polycycloalkanes, 2525

Conformation (conth4ed) ring enlargement in bridged bicyclic systems, 4867 selenium heterocycles, 4335 tetrabenzocyclooctatetraene, 4677 Copper compounds active form of catalyst, 3903 alkyl copper (1) complexes, 2803 aryl - , arylalkyne synthesis, 5209 carboxylates, with organyl halides, 491 ethoxylcarbonylmethylcopper, prep. of y,l-unsaturated esters, 1163 lithium dimethycopper, reaction with benzal and benzylic chlorides, 293 coumarlns calophynic acid, 27 15 euphorbetin, 601 furo - , archangelln, 3811 synthesis, 237 glabralactone, 217 1 is0 - , ring contraction, 3409 4-phenyl- and 4-aIkyl - , 3 187 robustic acids, 759 toddaculin, synthesis, 185 Cubanes 1, 8-bishomo - , rearrangement, 4913 homocubane bond reorganization, 4909 Cyanides 2azapropenoids, 2 cyanopyrazines, 477 1 decyanuration of succinonitriles, 1003 N-cyanoazlridines, ring opening, 4121 tetracyanoethylene with eucarvone, 3625 Cyclic compounds cycloalkenes, aromatization, 903 haloginocyclohexanones and halogenodecalones, long range coupling, 277 sulphones, cathodic cleavage, 1469 Cyclization reactions activated tosyl peptideq 4283 p-amino crotonic esters, 327 arenylphosphonic acids, thermal - ) 4977 2;(3-butenyl)-l-vinylcyclopentanol, 4973 cis-dienone-oximes, thermal, 3 13 diphenylmalodinitrile, photo - , 821

Subject Index

ix

‘Cycliition reactions (continued) Cycloaddition (continued) Cyclobutaned (confinued) elcctroreductivc - , acctylenic 2-phenyl-2-oxazolin4-one to tri-t-butyl-cyclobutene dicarbc+ halides, 453 alkene, 4039 xylic acid, 4483 cyclodeanal isoprcnoids, clectrophilic. 2 I75 polar - , electrophilic nature, cis, cis- and trans. trans-cyclodecap-ketosulphoxides, 3393 4969 1,6-diene, photocyclization, monoterpenoids, 243 1 6,6’-polymethylene-bis (4-methyl569 N-amidino hydrazonyl bromides 2-pyrone), 2247 3,4,9,10_cyclodecatetraenal, 7to aminotriazoles, 394 1 pyrroles, 4703 dione, stereochem., 3425 nitroso-alkene, 4287 A’S + n’ s, solvent effect, orbital 1, 1,4,4-tetramethyl-7-cycle oxidative, lead tetraacetate, 4179 interactions, 1401, 1405, 1409 decyl derivs, bimolecular oximes, neighbouring group systhiophenes to acetylenes, 5269 elimination, 23 tern; versus elimination, 1213, tropone with quadricyclene, [6 + Cycloheptanea 1217 i + 21 395,399 benzp[3,4]cyclobuta[1,2-b]cyphoto - , cis, cis- and trons, tronstroponoids with maleic anhydride, cloheptatriene, 4859 2685 cyclodeca-I , 6-diene, 569 ‘I-cycloheptadienyl cations, 4403 cyclohexenones, 2767 ynamines with CO,, carbamoyl and cycloheptanones, ring inversion, tris (triphenylphosphine)-rhodium and keto-alkoxy-ketenes, and 4331 chloride, 4375 alcoul-isocyanates, 113 1, 1135, cycloheptatriene, J, 6-addition of unsaturated acyl chlorides, 749 1139 phenalenylidene, 5089 ylides, giving dihydroindolizines, Cyclobutanes 3,4dichlorocycloheptatriene, 2585 3-amino- and 3-hydroxy-2,4mass spec., 5235 Cycloaddition diphenylcyclobuten-l-ones, heptanona-fulvalenes, 3523 alkyne photochem., metal carbonyis, 3347 iodolactones of bicyclo[ 2.2.11 1589 aminocyclobutyl methyl ketones, heptanes, with hydroxide ion, arylazirines to hetero-multiple 4663 1143 bonds, 4087 benzocyclobutenedione, bis-decarnucleophilicitieq 189 1-azirines with ketenes, 1353 bonylation, 5321 tropone, [ 6+2+2] cycloaddition azodicarbonyl compds. to alkenes, benzocyclobutenone, 1249 with quadricyclene, 395, 399 4713 pyrolysis and photochem., Cyclohexanes benzophenone to conjugated 3917 a-alkoxycyclohexanones, 2415 enyne, 2265 bissiloxycyclobutenes, 853 alkylcyclohexanones, reduction 2,4-cyclohexadienone DieleAlder cyclobutadiene, antiaromaticity, by propan-2-o1,637 dimers, 5 177 5113 benzocyclooctatetraene and cyclopropene dimerization, zeocyclobutanel, 2-diol, 857 benzocyclooctatriene, ring lite catalyzed, 23 I cyclobutanones, cis-jasmone inversion barrier, 665 diazomethane to hexatrienones, synthesis, 1233 3-t-butylcyclohexene, electre 4803 u, a-dichlorocyclobutanones, philic attack. 3527 dichlorocarbene to alkenes, 156 1 NMR, 1245 4-t-butyl thiacyclogexane, methyhetero - , functionally substidihalomethylene - , electrorelation, 4921 tuted piperidines, 1425 duction, 4899 cyclohexadienones, cycfopropylhomodiazepine synthesis, 3575 dihydro cyclobuta[b] benzothiomethy group migrations, 5 17 intramolecular [ 2 + 21, cyclopenphenes, 4597 cyclohexanones, two or three tadienone dimers, 303 dimethylsita - , 3495 chiral second spheres, 4275 isoquinolinium ylids with acety3,4diphenyLbenzocyclobutene, cyclohexene ring contraction, lenes, 3325 photochem, 547 5317 cyclohexenones, photocyclization, ketenes with Schiff bases, 3633 diphenylcyclobutenedione with 2761 methyl and phenyfulvene to tromethyl phosphites, 787 2, 3-diary1 cyclohexanones and pone, 2297 diquinocyclobutene, 145 1 oximes, reduction, 2251 2-methyl-2,4-hexadiene with ace naphtho[b] cyclobutenc, 2439 I-diazoethyC3-cyclohexen-1-yl tone, 1229 1-phenyl-cyclobut-1-ene3,4ketone, 1363 nitrones to arylisothiocyanates, dione, substitution, 3885 1, 2-disubstituted chlormethyl 4191 spirocyclobutanones, 2849 cyclohexenes, 109 1 0-alkyl thiobenzoates to alkenes, t-butyl clclobutadiene, 1025 dl-phyllostine and dlepoxydon, 4993 tetramethyl-1, 3-cyclobutane-segiospecific synthdsis, 5 I05 8-oxoheptafulvalene, 869 dione, 4 OZ oxidation, 3483 3ethylidene2, 2, 5, 5-tetrao-xylylene, bimolecular, 2443 tetmmethylcyclobutene, valence methylcyclohexanone, 1367 photo - ,3_ethoxyisoindolonc isomerism, 103 1 hexachloro - , isomerization, to alkene, 4035 tetramethylcyclobut-3ene, 4359 4807

X

Cyclohexanes (continued) I-methoxycyclohexa-1,4-diene and 1,3diene, 4 195 1-phenylcyclohexene, photolysis, 2663 Spiro-epoxy-2, clcyclohexadienones, 4205 tram-l, 4dichloro - ,4965 4-trichloromethylcyclohexadien~ one, semibenzene from, 1019 d-unsat. - , ketones, 4461 Cyclononanea 1,2_cyclononadiene, addition to dimethylketene, 1189 cyclononatetraenide with 3-subs pentacyanines, 1021 dibenzocyclononatetene phosphonium ylide, 3361 Cyclooctanes 2,4-cyclooctadienone, photochemical dimerization, 1349 2,4-cyclooctadienone system, ring inversion, 57 7,8dichlorocycloocta-1, 3,5Gene, isomerization, 3661, 3665 I-oxacyclooctan-S-one, conformation, 36 13 tetrabenzocyclooctatetraene, inversion barrier, 4677 ring inversion, 4 187 Cvclooentanes 2-(3-butenyl)-l-vinylcyclopentanol, 4973 t-butyl cyclopentadienone, 1025 cyclopentadienide with 3-subs. pentacyanines, 1021 cyclopentadienone dimers, photothem., 303 cyclopentanone in prostaglandin synthesis, 3337 4-hydroxy-2-cyclopenten-l-ones, synthesis, 3735 3-methylcyclopcnt-2-en-2-ol-lone, 4655 pentanona-fulvalcncs, 3523 Cyclopropanea alkyl diazopropionates with alkencs, 53 alkylidcnc - ,4213 ally1 - , 2411 benzocyclopropanc, 3917 his-2, 3-diphcnylcyclopropcnc anhydrides, 1579 bis-(tctraphenyl-cyclopcntadicnyl), 5231 carbonyl group conjugation, I, ldicarboxylatcs, 997 chrysanthcmyl and prcsqualenc alcohols and cstcrs, NMK shift rcapcnt. 4027 (cyan-aryl-methylcnc)-cyclopropcnc. 3883

Tetrahedron

Letters 1972

Cyclopropanes (continued) Cyclopropanes (conrimed) cyclopropanation of alkenes, 1465 unsaturated, ring expansion, cyclopropanones, (Y,ar’-dibromo1605 ketone reduction, 4079 vinyl - , with diiron nonacarbonyl, cyclopropenes, dimerization to 5325 tricyclohexanes, 23 1 1-vinylcyclopropanols, thermal reaction with enamines, 3965 ring enlargement, 2849 rearrangement, 42 13 synthesis, 937 cyclopropenium ions, acetylenes from, 3765 cyclopropenones, 44 15,44 19 Deacetylation ring opening and reaction with steroid acetates on 44, 3349 enamines, 2603 Dealkylation cyclopropenylketones, 4483 quaternary ammonium ions, 2167 cyclopropylcarbinyl-cyclobutylDeamination homoallylrearrangement, 43 1I 2-aminomethylnorbornan-2-ols, cyclopropylcarbinyl mesitoates, 4867 reductive rearrangements, 1475 a-substituted bicyclic nitroso cyclopropyl 1, 2-diketones, compd., 7 photodihydrodimerization, Decarbonylation 1307 benzocyclobutenedione, 5321 cyclopropyl group, migratory photo-chelotropic, mechanism, aptitude, 3249 1049 cyclopropyl radical, stcreochem. Decomposition and electrocyclization, 4759, cyclic azo compds., 1225 4765 3-diazo-2-norbornanones, 1069, 1,2-dialkyl-3-carbomethoxycyclo1073 propcnes, 3367 dimethyl diazomalonate, copper diethoxycyclopropenone, 127 I catalysed, 3903 1, 1’-dihydroxy bicyclopropyl, exe-7-azidobicyclo[4.1.0] heptane, 4593 3933 I, I’-dimethylbicyclopropenyl, N-nitroseN-methylurea, base inisomerization, 3509 duced, 5 147 diphenyl - , 1155 organomercury derivs. free radical, diphenylcyclopropene, conden2281 sation with phcnylmalodinisulphonium betaines to epoxides, trilc, 3883 3313 diphenylmethylenecyclopropane, Dehydration 3901 alcohols, mechanism in HMPA. addition of N-chlorosulphonyl 165 isocyanate, 155 1 diethyl azodicarboxylate and tri1, 3_diphcnylpropenone, methoxyphenylphosphine agents, 1279 mercuration, 4709 1,5-diphenil-1-benten-3-01 by clcctrocyclic rearrangement, 4799 polyphosphoric acid, 3743 endo-8-tricyclo[3.2.1.0’V4] octafructose, 4813 none, 4095 vinylogous ureas, 15 19 formation in acid cat. reaction of Dehydrogenation eucarvon, 3625 cycle - , uliginosin B, 4787 fused, configuration inversion Demethylation during ring opening, 22 1 dimethoxyindoles, 393 Rem-dimethyl - , 3781 Deoxygenation -I-methylcyclopropenc with trialiphatic nitroso compds, with alkylboranes, 4627 trialkyl phosphites, 4059 methylenecyclopropenes with tritylthionitrite, 3405 ynamines, 3969 Deuteration oxaspiropentanes, 887 steroidal alkaloids, 3499 photooxidative cleavage, 9 Diamantanes pyridazincs from methylcnecycloI- and 4-chloro - , conformation, propcnes and hydrazine, 373 I 1547 ring opening, regcospccificity, Diazines 4577 cstcr hydrolysis catalysis, 189 tri-t-butylcyclopropcnyl ____ 3293

azidc,

N-oxidcs, electrochemical dation, 427

oxi-

xi

Subject Index Diaziridines diphenylketene and, 3999 oxidation of cyclic hydrazines, 245 1 Diaziiines thermal destruction, chelotropic reaction, 4247 Diazo compounds alkyl diazopropionates, synthesis, 53 diazocyclopentadienes, 3479 I-diazoethyl-3-cyclohexenI-yl ketone, 1363 diazomethane, addn. to aromatic sulphines, 2293 cycloaddition to hexatrienones, 4803 diazomethane-d, , 1501 3-diazo-2-norbornanones, decomposition, 1069, 1073 dimethyl 2, S-bis(diazo)-3,4-d& ketoadipate, 4281 dimethyl diazomalonate, copper catalysed decomp., 3903 ethanes, photochem., 2469 ketones, pyrazole formation, 4979 tris-o-diazoketones, cyclization, 2589 Diazonium salts 5-chloromethyl-3-ethoxycarbonyL l-phenylpyrazole, 3637 copper catalysed decomposition, 3637 reduction, ‘sC-polarization, 258 1 Dienea arsabarrelene, 396 1 bicycle [ 3.2.11 octa-2, 3-diene, 2871 1, 3-bishomoadamantadiene, 4887 butadienepropylene codimerization, 4775 buta - , reaction with amines, &and effects of catalyst, 2773 reaction with diethylamine, 4197 substituted,photoelectronic spectra, 2739 cis-dienone-oximes, thermal cyclization, 3 I3 conjugated, bromohydrin formation, 1057 cyclopentadienone dimers, photothem., 303 I, 2_cyclotridedadiene, dihydroboration, 4871 dimerization of I, 3 - , 1457 1-methoxycyclohexa-I, 4 - ; to a 1, 3-diene, 4 195 2-methyl-2,4-hcxadiene, photocycloaddn. to acetone, 1229 4-methyl-l, 2-hexa-diene-5-yne, Cope rearrangement, 357 I non-conjugated dienones, photothem., 3679

Dienea (continued) norcaradienes, 869 octa - , catalysed formation, 167 phenol-dienone isomerization, 4929 phosphacyclohexadienes, 4925 stereoselective telomerization, 4009 ‘I-substituted norcaradienes, 3451 sulphonamides, photorearrangement, 3321 truns-l-subs-l, 3-buta - , CNDO/ 2,3329 Dimerization 2-benzal-4-phenylpseudooxazolone-5,3347 I-benzyl-1,4-dihydronicotinamide, 4883 co - , propylene and butadiene, 4775 cyclic, ethynyl ketone, 3157 2,4-cycfooctadiene, 1349 cyclopropyl I, 2-diketones, 1307 diacetylanhydrouridine photothem., 4667 1, 3-dienes, nickel-ligand catalyst, 1457 3,4-dihydro-1,9, 10(2H)anthracenetrione, 73 1 formaldehyde alkylhydrazones, 949 indohzines, 2607 isoeugenol, 4955 isoprene with magnesium, 2833 methyl crotonate, 4477 photodimers from naphthalenes, 321 S-(+)-l, 3-diphenylailene and triphenylallene, 1265 Diils 3-alkyl-truns-1, 2- , 4031 cis-1, 2-glycols, afkene oxidation, 4907 cyclobutane c&l, 2-diol, 857 steroidal ene-dials and triols, 4501 trans-1, 2 - , prep., 2845 vicinal. 4435 Dioxetanes aoamantyhdeneadamantane peroxide, 169 3,4-his-biphenylene-I, Z;dioxetane, 5143 1, 3-dioxenium compds., 3973 Dioxolanes I, 2-dioxolanes, photolysis, 1357 free radical isomerization, 1487 Dioxoles benzo-I, 3 - ,4217 dioxolenium ions intermediates, 4497 Dipole mesomeric dipole moments, 46 13 moments of ethoxyethene, 2243

Distortion ethylene, 479 DithiMes I, 3-dithianes, 4-hydroxy-2-cyclepenten-l-ones synthesis, 3735 Diynea diphenylbuta - , pyridme and pyrrole synthesis, 3487

Electrochemical reactions anthracenes, anodic oxidation, 1449 aromatic N-oxide oxidation, 427 carbon-halogen bonds, reduction, 1371 cathodic cleavage of cyclic sulphones, 1469 cathodic synthesis involvina- CO,, _4809 a, cr’-dibromoketones, reduction, 4079 1, Zdithiolylium ions, cathodic reduction, 767 hybrid type redox systems, indoles, 643 methoxybiphenyl cation radicals, 2271 Michael-addition, 965 oxidation, aromatic hydrocarbons, 2419 benzidine rearrangement, 3675 perchlorodiphenylmethyl radicals, 1497 radical identifications, 5009 reductive cyclization of acetylenic halides, 453 salicylic acid reduction, 3433 specific ion electrodes, 5 13 4,5,9, lO-tetraazapyrene prep., 3643 tri-t-butyl-cyclobutene dicarboxylic acid, 4483 Electrocyclic reactions I, 2-dimethylenecyclohexanes, 367 elimination of ethylenedione, spin multiplicity, 3897 non-benzenoid aromatic compds., 4859 Electronic effects free radical addition of thiols to norbornenes, 2719 Electron spin resonance alkyl radicals, halogen effects, 2427 alkylsulphinyl and alkylsulphonyl radicals, 4075 amido radicals, addition to alkenes, 535 ITground state, 183 hindered rotation, 1413

Subject Index Esters (conlinued) yeast hydrolysis, 243.5 Ethers allylic - , with allyllithium, 2411 o-amino - , epimerization, 3773 aryl - , anodic coupling, 227 1 benzoin, photochem., 4755 bergaptyl and isobergaptyl - , 3811 enol - , iodination, 3629 with N-haloimides, 4055 halogenated phenetoles, mass spectra, 22 11 imino - ,2459 macrocyclic, 56 1 p-methylanisole, ambident base, 1477 phenol - , dealcoylation, 25 I reduction by 2n/HCl, 725 synthesis, phase transfer catalysis, 4521 Exchange reactions ester - , photolysis of gem-chloronitrosocompds., 593 Excited states carbonyl donor partial chargetransfer interactions, 2163 phenyl - and thienylpyridines, basisity, 233 Extrusion reactions acetylenes from cyclopropenium ions, 3765 ‘C-spin lattice relaxation, 3709 cyclohexadienylcyclopentadienyl iron, hydrogen transfer, 2625 endo- and exe- 1, 2+-aminotetramethylene)-ferrocene, 2885 ferrocenyldihydropyridine, oxidation with DDQ, 93 ferrocenylmethyl group migration, 3535 from fulvenes, 4639 fulvenes, 3379 methoxy - , electrophilic substitution, 5217 ring basicity, 269 Stobbe reactions, 5005

Flavones 5_carboxymethylflavone, 3419 (+)-hepta_O-methylfukugetin and heptaQmethylsaharanflavone, 4383 lipophilic bud excretions, 797 NMR shift reagents, 4 125 stachyoidin and tephrodin, new, 703 Fluorenes hydro - , from I-abietic acid, 4507 Fluorescence charge transfer complexes, 3363

...

Xlll

Fluorination Free radials (contizued) alcohols, phenyltetrafluorophospropellane - ,525 phorane, 847 tetraphenylhydrazine oxidation, Fluorine compounds 5009 thiacyclohexyl - , transannular fluoroalkenes, with ethanolamine, participation of S atom, 339 3957 thiol addn. to norbornene, 2719 fluorobenzenes, nucleophilic trapping efficiencies, 981 photosulostitution, 685 2,2, 2-triphenylethyl, rearrangeperfluoropiperidine with phenols, ment, 3309 mechanism, 5 169 Formylation Fulvalenes annelated nona - , 721 piperidine, 173 PMR shift, Me detection on C-OH, diphenylheptatriafulvalene-3,4dione, 2227 4865 Fragmentation pentanona - and heptanona - , aziridinium ylids, 3827,4659 3523 /3-chloro- and fl-tosylketals, 5225 tetrabenzo[5,7] fulvalene, spatial endo-&tricyclo [ 3 .2 . 1.O”* ] octastructure, 273 FlllWlW none, 4095 dibenzopenta - , isomerism, 3379 epoxide, 7 17 fulveneallene synthesis, 1249 halogenated phenetoles, mass hepta - ,3969,4403 spectra, 2211 6-hydroxy - ,496l longibornane system. 7 15 methyl - and phenyl - cyclooxadiazolines, 3 169 addition to tropone, 2297 Free enerev 8-oxohepta - ,869 plots,Enearity deviations, 753 with 2-methoxytropones, Free radicals alkyl - , conformational effects 4379 of halogen, 2427 Fungus alkylsulphinyl and alkylsulphonyl, antheridiol. funeal sex hormone. ESR, 4075 2673 ‘ amido - , ESR evidence for n sexhormone, 791 ground state, 183 ascofuranone, terpene, 2541 hindered rotation 14 I3 chlorosis inducing metabolites intramolecular reactions, 5 3 1 from, 3789 aromatic anion - , 3447 isomerization of farnesol and 1,4-arylradical rearrangement, epoxyfarnesol, 5 101 1567 metabolite, viridominic acid, 199 7-azabicycloheptyl-N-oxyl derivs, pigment, grevilline, 4895 3317 sesquiterpene dialdehyde extracts bridged bromoalkyl - ,3 17 NMR-simulation, i 105 cation and anion for thieno[ 3, 2Furans b] thiophen, 3847 2-alkyl-3-hydroxydihydrobenzocyclopropyl - , stereochem. and furans, 2873 electrocyclization, 4759, benzofuranoid systems, synthesis, 4765 237,241 diaryliodonium alkoxide decomp., benzofuranones with benzofurox3301 ans, 3653 fragmentation and rearrangement, 2,5-dihydro-2,4-disubs -, 4071 1,2-dioxolanes, 1357 farfugin A, absolute configuration, Crignard reagent formation, in5251 volvement, 281 fraxinellone, 3401 isomerization, dioxolane, 1487 furanoeremophilane+& 108diol, isocyanide attack, 3699 skeletal rearrangement into isoeugenol dimerization, 4955 farfugin A and B, 5255 methoxybiphenyl cation - , 2271 2-(hydroxyacetyl) - ,4813 nitroxides, phosphorous containoxidation, 6-hydroxy-ZH-pyraning, 4449 3(6H)-ones, 133 preservation of radical funcsesquiterpene, NMR, 85 1 tion, 555 tetrahydro - , alkyl lithium addn. organomercury derivs. of tin, deto alkene, 4029 camp., 228 1 trichloroacetyl isocyanate and, oxiranyl, configurational stability, NMR, 5 167 981 perchlorodiphenylmethyl - , 1497 Furoxans benzo - , with set-aliphatic phenylbromopropane photolysis, amines, 5365 1571

xiv Furoxens (continued) dibenzoyl - , with phenylacetylene. styrene and stilbene, 3469

Halogen compounds (continued) immonium salts and enamines, 4743 johnstonol, epoxide from red alga, 195 Geometry p-ketosulphonium halide - copper 2-amino-firms-2-decalin-carboxylic halide complexes, 407 acids, 4157 Nhaloimides, with enol ethers, dibenzopentafhlvenes, 3379 4055 &eliminations, base promoted, polyhaloadamantanes, 3 19 1 2621 rotation barriers in subs. ethanes, ligandeuropium complexes, 3539 2779 Michael addition, 4625 Helicenes saturated ‘flat’ carbon, 4315 double, structure and config. by tetrahedral coordinates, 1441 INDOR and NOE, 27 3 1 Glucolysis hetero - , 763 nitriles, anhydrous, 4643 assignments, 2839 Glucoside nonracemic - , mechanism of synlinarioside, chlorine containing - , thesis, 2195 419 thermal racemization, 3707 Glycosides Hemiketals apiofuranoside anthraquinones, cyclic - , macrolide antibiotics, 5013 5053 derivs for synthesis, 3461 High pressure geniposidic acid, iridoid glucoside, decomposition of cyclic azo com5125 pds., 1225 methyl 4,6-di-O-acetyl-2, 3-dideoxyhexachlorocyclohesanc isomcriP-D-ethythro-hex-2_enopyranozation, 4807 side, 5 I37 p-nitrophcnylazotriphenyhnctl~anc, platycodoside C, 365 1 viscosity and pressure tests for Griid reactions cage return, 1221 acetoximes and. giving amines, Hormones 1007 anthcridiol, fungal sex - , 791 allylic Grignard addn. to C = C, fungA sex, anthcridiol, 2673 2285 plant growth - . pibbcrellins, 4299 bialkyls and biaryls from Grignard Hydration reagents, 2193 hcxamethyl (Dewarbenzene) oxide, formation, CIDNP evidence for 3137 radical pathway, 281 Hydrazides ketone synthesis with acid chlorN’, N’-diary1 - , 321 1 ides, 467 Hydrazines pyridineN-oxide, 31 1 I, 2-bis-benzencsulphonyl-1, 2sugar cstcrs of a-kctoacids, 4855 dicthoxyhydrazine, temp. depcndcnt NMR, 571 cyclic, oxidation, 245 1 Halogen compounds hydrazinium salts, rearrangements, acetylenic - , clectroreductive 319 cyclization, 453 N, N-disubs, with 2_phenacyldime2-alkyl halides, p-elimination, done, 1467 2621 tetraphenyl - , radicals from, allylic and benzylic halides, 4339 5009 carbon-halogen bonds, electrolytic Hydrazones reduction, I 37 I arylhydrazonates, rearrangement, copper carboxylatcs with, 491 3211 dihalocyclobutancs, 4899 erythromycin - , with nitrous halo~cetylcnes, NMR, 4023 acid, 29 haloaromatics, reaction with cleformaldehyde alkylhydrazones, mental sulphur, 1283 dimerization, 949 halogenocyclohcxgones and rearrangements, from aryl benzohalogenodccalones, long range ates, 1299 coupling, 277 Hydride shifts a-haloketones, synthesis, 4661 intermolecular, Spiro adamantanes, halophosphincs, with aldehydes, 1179 3953

Tctrahcdron Letters 1972 Hydroboration cnolatcs, 2845 hexamethyl, 3 I4 I Hydroformyiation alkynes, 3455 Hydrogenation allenes, selective, I39 I catalytic, stereochcmical criteria, mechanism. 5 I55 2-furfuraldoximc, 4099 norbornadicnc, 2503 Hydrogen bonding enantiomeric acids and amines, 3873 2-haloethanols, NMR, 3547 to n-systems, 3 129 Hydrogen shifts competitive sigmatropic - , bicyclo] 3. I .O] hex-2-en-en&-6carboxaldehydes, 125 Hydrogen transfer aminc-iminc hydride transfer, 2807 cyclohcsadicnylcyc1opentadienyl iron, fragmentation, 2625 D-glucose to 2-(hydroxyacetyl)furan, 4813 formyl compds. to 0, p-unsaturated ketones, 1015 intramolecular, long chain alephatics, 5073 Hydrolysis acetanilides, mechanism, 5241 esters, by yeast, 2435 diazine catalyzed, 189 p-nitrophcnyl acetate, 4581 Hydroxylamines 0-aryl - , addition to dimethyl acetylenedicarboxylate, 394 I Hydroxyl group activation of primary in glucopyrannoside, 5001 concentration dependence of proton multiplicity, 3543

Imidazoles acetic anhydride reagents, 4723 1, 2-disubstituted imidazole-4,5dicarboxaldehyde, 2 173 1, 2, 4-oxadiazo1e rearrangement, 4959 Imides alkylation with chloroformate esters, 3921 aminimides, Curtius rearrangement, 289 N-alkoxyisosulphobenzimides, photochem, 3289 N-(alkyl and arylsulphinyl)-phthalimides, 5313

xv

Imides (cofr/irrrcc~/) N-cl~lorol~oly~~i~Ilrimidc,specific chlorinalion, 5 I73 N-halo - . with cnol cthcrs, 4055 phthalimidc system. photochem, 4517 reduction, giving bridged nitrogen hctcrocyclcs, 4493 Imines anti-Bredt’s rule, 335 arylketoimines, configuration, 4491 benzylidene aniline complexes, 459 bicyclic bases, 3987 chromanone - , condensation, 1445 C-imidoyI-C-cthoxyketcnimines, 1519 conaninc derivative, 505 cycloaddition to ketenes in SO,, 3633 formation, primary amines with lithium reagents, 281 I heteroaromatic N - , 4133 iminoketones, heterocyclization, 2781 inversion barrier, 2655 ketimine derivs of amino acids, peptide synthesis, 226 I . malonodialdehyde-de-nentadeuteroanil, 371 . N-acylketimines, Wittig-Horner, 4487 Naroyldiphenylketimines, photochemical reduction, 105 3 N-benzhydryl - ,4949 oxidation with lead tetraacetate, 19 phthalanylideneammonium salt transformations, 2711 thiocarbonyl - , 1159 Immonium salts di - ,85 o-halo - ,4743 phenoxymethylene - ,4217 lndazoles 3-benzyl-3-cyano - , rearrangement, 4529 indazoles, pyrolysis, 3207 N-acyl -

,4533

Indenes carbonium ions to diphenylacetylene, 2869 indencones, 27 I 1 Indolenines a-chloroisatin with mcthancthiol and 1, 2-cthanedithiol, 307 Indoles

alkaloids, biosynthetic incorporation of L-leucine, 2659 from oxindole alkaloids, 108 1 3-alkyl - , electrophilic substitution, 5277

Indoles (corhnued)

Iron compounds

3-amine-4-keto-4,5,6, ‘I-tetrahydro - , 1467 5-aza - , 2857 benzo [c] indole, new route, 4295 bis(3-indolyl-)-3H-indolidenemethane, 3807 2-carbethoxy-l-methyl, 3949 2, 3-dihydrocyclopent[b] indole, 953 dimethoxy - , demethylation, 393 1 hybrid type redox systems, 643 imidazole-Ac,O reagent and, 4723

carbonyl induced olefin coupling, 2815 diiron nonocarbonyl with vinyl cyclopropane, 5325 iron carbonyls with heterocyclic compds., 3 183 Isocyanates chlorosulphonyl - , addn. to Qand p-pinene, 495 I cycloaddition of ynamines, 1139 N-chlorosulphonyl - , 3901 addition to diphenylmethylenecyclopropane, 155 1 organometallic, thermolysis, 1065 phenyl - , stability in DMSO, 2843 trichloroacetyl - , with furan and pyrrole. NMR, 5167 Isocyanides free.radical attack, 3699 tosylmethyl - with Michael acceptors, pyrrole synthesis, 5337 IsofIavans new, from Phaseolus vulgaris infected with tobacco necrosis virus, 4175 Isoindoles cyan0 - ,4717 3&hoxyisoindolones, 4035 Isomerism geometrical, dibenzopentafulvenes, 3379 rotational, 3-p-D-glucopyranosyl6-metllylurdcils, 3911 tetramethylcyclobutene, 103 1, 1035 valence, 2, 4-cyclohexadienone and bicycle [ 3. LO] hcxenone, 2735 Isomerization 2- , 3-, and 4-pyridylcarbenes to phenyl nitrene, 2239 I-chlorohomotropylium salts and 7, 8-dichlorocycloocta-I, 3,5triene, 366 1 cis. trans-4-methyl-2-oxo2H-1, 3, 2-dioxaphosphorinanes, 309 coumarin ring - , 2 I7 1 1, 2-diazepin anion, 489 I dibenzo (CH),,-hydrocarbons, 2573 1, I’-dimethylbicyclopropenyl, 3509 cu-ethylenic alcohols, 241 1 exo/endo-5-methoxy-bicycle [2.1.0]pentanc, 359 epoxyfarnesol and farnesol, 2, 3double bond, 5 10 I hexachlorocyclohexane, 4807 long distance, 4739 7_oxanorbornadienes, 4961

lndolines

N-acctyl - ,503l N-acyl -. photolipis, 5031 I-oxide, photochem., 3215 lndoliiines dihydro - , 2585 sigmatropic reactions of spiropyrazolines, 3479 vinyl - , dimerization, 2607 Infra-red spectra acctamide-phenol interaction, 4457 alkylbenzcne-aluminium chloridehydrogen chloride complex layer, 5259 boron trifluoride cyclanoncs, 424 1 C = C = N absorption, 15 19 cyclanone-Ti Cl., complexes, 4563 I, I-dioxo-1, 2-thiazctidine. 213 low temp., 2, 4-cyclohexadicnone valence isomerism, 2735 2-(5-phenyl-1, 2-dithiole-3-ylio) phenolate, 4687 Insecticides DDT, dchydrochlorination, 2887, 2891 organo-phosporous, 4245 Insertion reactions

benzyne with alkylbenzenes, 4 14 1 Inversion configumtion in fused cyclopropane ring opening, 2 11 ring - , cycloheptanones, 4331 Iodine compounds diaryliodonium alkoxides, decomp., 3301 diaryliodonium salts, alkalein photolysis, 4793 diphenyliodonium salts, photolysis, 3739 enol ether iodination, 3629 iodine thiocyanates to alkenes giving thiiranes, 3567 iodo-methylation and iodo-propenylation, 2743 Ions

base ion-oairina in bimolecular eliminations, 23, 265 carboxonium - , 5225 ion pair extraction, 473 pairing, quaternary ammonium salt elimination, 3439

Tetrahedron Letters 1972

Xvi

Isomedzation

(continued) perchloro+methylene-bicyclo[ 3.2.0) hepta-2, Cdiene, 2609 phenol-dienone, 134 1 2-phenyl-benzazepine alkaloids, 4431 thiophenes, valence bond, 1429 tricvcloI3.1.0.0”* 1hexane. 3757

I8onitie.s-

urea and urethane synthesis, 4263 lsopIr=~ electrophilic cyclization, 2175 1, Zlinking of isoprene units, 3371 magnesium and - ,2833 ISO&Wlill~

Isoxazolinea (continued) photoinduced nitrite rearrangement, 661

Ketals

&chloro- and P-tosyl - , fragmentation, 5225 ethylene - , generation from alkenes, 3595 thio - , cleavage, 1085 Ketenes

autoxidation, 3397 C-imodoylC-ethoxyketeneimines, 1519 cycloaddition, of ynamines, 1135 to Schiff bases in SOZ, 3633 with I-azlrines, 1353 dichloro - , adducts with alkenes, NMR, 1245 dimethyl - , addition to 1,2-cyclononadiene, 1189 addn. to 1, 3-dimethyl allene, 2499 dipItt9;I - , with diaziridine,

aminobromo - , ring fission, 47 17 I-benzyl-1, 2dihydro - , rearrangement mechanism, 5373 I-benzyltetrahydro - , alkaloids, ’ 2215 bisbenzyl - alkaloids, diphenyl ether attachment, 423 dihydro-5, 6-pyrrolo[ 2, l-a] isoquinolines, 278 1 3, lob-dihydropyrrolo[ 2, l-a] isoquinolines, 3325 improved route, 4789 ochotensine type synthesis, 4847 keto - , generation and reactivity, synthesis, o-subs benzylamines, 3703 3149 photochem generation, 3443 lsothiiOles seleno - , photolysis and therbenzo - , 3289 molysis, 445 S-hydroxy - , ring synthesis, 327 Ketones Isothiocyamtes achiral - , redudtion, steric conaryl - , cycloaddition to nitrones, trol, 687 4191 a-alkoxycyclohexanones, 2415 phenyl - , N, N, N’-trimethylbenalkylation, 929 zamide, 4699 cu-allenic, 3257 Isotope effects with trivalent phosphorous dehydrochlorination of DDT, derivs., 149 2887,289l aminocyclobutyl methyl ketones, deuterium, NMR, shift reagent in4663 duced, 879 ammonia oxidation in presence of, kinetic deuterium - , homocubane, 529 4909 azibenzil with SO,, 4979 monoterpenoid cyclization, 243 1 benzophenone, hydrogenolysis, lacrtope incorporation 691 2’- and 3’0trityluridine, 3345 photocycloaddition to enyne, 2-butyl cation, hydrogen bridging, 2265 1241 photoreduction product, 4949 carbon-halogen bond electrolytic triplets with norbornadiene reduction, 137 1 and quadricyclene, 5345 chlorine-36,807, 811, 817 bicyclo[3.1.1] heptanone, 4573 diazomethane-d, , 150 I C, - C, cyclanones with BF, , UV, n-butyl bromide “Br, photobro 4553 mination, 3 17 circular dichroism, front octant tritium into aurcotinc antibiotic, effects, 1315 4875 cis-decalin-2, 6-dione synthesis, ISOxaZOleS 137 isoxazolo[ 2, 3-a] pyridinium salt condensation with enolatc ylids, rcarranprmcnt, 609 933 Isoxazolines convcnicnt prep. from alkenes, 4-arylidcnr-isoxazotine-5-ones, 4993 NMR, 1147

Ketones (continued)

cyclic - , BF, compleies, IR study, 4241 cycloalkanones with IIMPT, 929 cyclopropyl 1, 2-di - , photodehydrodimerization, 1307 desoxybenzoins, photochem., 3411 1, 4-di - , synthesis, 1233 diazo - , pyrazole formation, 4979 a-diazo - , with benzyne and alkyncs, 4533 I-diazoethyl-3-cyclohexen-l-y1 - intramolecular cyclization, 1363 (Y,o’dibromo - , electrochemical reduction, 4079 dimethyl 2,5-bis(diazo)-3,4-diketoadipate, 428 1 diphenylcyclobutenedione with methyl phosphites, 787 enamino - , photochem., 2513 cu-epoxy - , reduction, 437 1 u-halo - , synthesis, 466 1 hydrogenolysis, 3 115 imino - , heterocyclization, 2781 a-keto-carbonium ions, 2561 ketoenamines, config., 3603 ketoketenes, generation and r6 activity, 3703 P-ketosulphonium halide-copper halide complexes, 407 macrocyclic, 3691, 3695 mass spectra, containing pyridyl groups, 705 u-morpholino - , 2597 r-nitro - , conversion to ydiketones, 1331 non-conjugated dienones, photothem., 3679 olefin coupling by iron carbonyl, 2815 2-phenacyldimedone, with hydrazines, 1467 prep., vapour phase alcohol oxidation, 257 reduction to secondary alcohols with thiourea dioxide, 343 steroidal epoxy - , 783 strained tricyclic, 3555 synthesis, niw, 2803 using insol. polymeric carbodiimide, 3285 via Grignard reagent - acid chloride condensation, 467 terminal alkene oxygenation, 5273 (n, n*) triplet, with benzyl disulphide, 3925 tris-a-diazo - . cvclization. 2589 ci, @Ut%ttU&d, 3-alkyd-trans1, 2-diols from. 403 1

Subject Index Ketones tcorrrinucd) ‘%?NMR. CNDO correlations, 565 hydrogen transfer from formyl compds.. 1015 p, y-unsaturated - , free rotor effect, 1367 photochemical double rearrange ment, 677 &unsaturated-ketones, 4461 Kinetics alkene esterification, catalytic, 2647 allene dimerization, 1265 aromatic resonance energies from equilibrium data, 5019 benzyl disulphide with (n, n*) triplet ketones, 3925 chloroformate esters in benzene, 957 competitive sigmatropic hydrogen shifts, 125 cycloadditions, solvent effects, 1401,1405,1409 dehydrochlorination of DDT, 2891 dinitroalkenes with KCN, slow ElcB elimination, 3511 epirnerizatjon of pentacovalent P, 4367 heteroarylmethyl derivs, solvolysis, 3889,3893 hexamethylDewar benzene, protonation, 3 197 homocubane reorganization, Michaelis-Menten. 4909 iodination of end ethers, 3629 micelles influence on rates, 4221 monoterpenoid cyclization, 2431 nitration of dimethylphenylsulphonium methyl sulphate, 17 nucleophilic reactivity, 4585 nucleophilic substitution of thiophenes, 402 1 1, 3-OxathioPdne ring opening, 2569 o-xylylene cycloaddition, 2443 photo-Fries rearrangement, 1575 quaternization of hindered amines, 3857 solvolysis rates in fluoroalcohols, 3617 tricyclo( 3. 1.0.02Y4] hexane, therma1 isomerization, 3757

Lactams CD and abs. config. of p - , 2793 cis-p-lactams, 2823 p - , formation, 409 1 shift reagent on diastereotopic protons, 3599 synthesis, 531, 535

xvii Macrocyclic comjrounda (continued) Lactones ethers and thioethers, 56 1 benzo$-propio - ,3443 pentadentate macrocyclic ligands, benzyl ether - , catalytic hydro4589 genolysis, 1123 polyaza-macrobicyclic compds., confertolide, sesquiterpene, 207 4557 daphnilactone A, 1275 Magnesium compounda dihydroalantolactone, 4843 aromatic carbonyl compds. with y-dodica - , from Rove beetles, trimethylchlorosilane/mag4635 nesium, 75 fraxinellone, 3401 isoprene and, 2833 iodo - , of bicyclo[ 2.2.11 heptanes, Mass SDectza 1143 apiofuranoside anthraquinones, a-methylene-y-butyro - ,2489, 5013 3375 2-arylamino-2-thiazolines, 15 2 1 perhydrolysis, 2669 benzyl amine and p-aminotoluene, peroxyvalerolactone, photolysis 1109 and thermolysis, 3483 ar-bisbalolone, sesquiterpene, 1295 sesquiterpene - , NMR, 621 cathanneine, new indole alkaloid, 3-succinimide-5,6-dimethoxy89 phthalide, 1197 cyclohexadienylcyclopentadienyl swazinc, Spiro dilactone alkaloid, iron, 2625 707 3,4-dichlorocycloheptatriene, 7-syn-6-ctrdo-dihydroxybicyclo 5235 [ 2.2.11 heptane 2-endo-cardirect analysis of daughter ions, boxylic acid-a-lactone, 35 1 2, 3_dihydrobenzoxepin, 4503 tctracyclic gibberellin, 3115 ethylenedione spin multiplicity, thiolo-7 - , CD, 3165 3897 Lead compounds halogenated phenetoles, 2211 acetate, oxidation of imines by - , isoeugcnol dimers, 86 1 19 ketones and diketones containing Ligands pyridyl groups, 705 effects, rhodium catalysed reaction micranthine, bisbenzylisoquinoof butadiene with amines, line alkaloid, 33 2773 onium compds., 3193 pendadentate macrocyclic - ,4589 4-phenyl- and 4-alkylcoumarins, tetrapyrrole, 3803 3187 Lignans pteridines, 3219 isoeugenol dimers, photooxidation, rauwolfia alkaloids, 1563 861 small peptides, pyrolysis methyleptostachyol acetate, insecticidal lation and esterification, 4621 properties, 653 sugars, MW determinations, 4827 new from gmelina orhorea, 2 179 Mechanistic studies nor - , (+)-trimethylsequirin C, acetanilide hydrolysis, 5341 3849 alcohol dehydration in HMPA, 165 Lipids alcohol oxidation by AgCOs, 4445 triglycerides, NMR, 2533 allylic Grignard addn. to C = C, Lithium compounds 2285 allyllithium reagents, 1471 aromatic nucleophilic substitutibn, chloromcthoxymethyl lithium, 613 alkene addition. 4029 aromatic ring contraction, 2235 dichloromethyl - ,‘4661 benzidine rearrangement, 3675 lithium di-isopropylamide, regeoI-benzyl-1, 2-dihydroisoquinoline snecific metalation. 3507 rearrangement, 5373 primary amines and - ‘, 2811 catalytic hydrogenation, stereo chemical criteria, 5 155 chloroformate esters, reaction in benzene, 957 2,4-cyclooctadienone, photoMacrocyclic compounds chemical dimerization, 1349 I, 5,9-cyclododecatrienes, boron dimerization of 1, 3-dienes, 1457 promoted epoxidation, 5093 @eliminations, driving force, 2759 1, 2_cycIotridecadiene, dihydroene reaction, irrelevance of azide boration, 487 I trapping, 45 dehydroannulenones, 3691, 3695

...

xv111

Mechanistic studies epimerization of a-aminoketones, 3113 formate and oxalate as nucleophiles, 111 glycolysis of nitriles, 4643 indazole pyrolysis, 3207 isocoumarin ring contraction, 3409 p&tam formation, 4091 nitration of dimethylphenylsulphonium methyl sulphate, 17 nonracemic helicenes, synthesis, 2195 ortho- and pum-fluorination, 5 169 o-xylylene cycloaddition, 2443 phase transfer catalysis, 4521 photo-cheletropic decarbonylation, 1049 Prim reaction, oxetane intermediate, 2797 rearrangement of furanoeremophilanedp, 1013_diolinto farfughr A and B, 5255 salicylic acid, electrochemical reduction, 3433 n4 s + rr’ s pericyclic reactions, 1405,1409 stereoregular polymerization, 1359 sulphonium betaine decomo.. _ -3313 troponoid-maleic anhydride cycloaddition. 2685 Q, p-unsaturated ketone red.“, (steroid), 46731 Mercury compounds aminomercuration, morpholine synthesis, 4013 dipivaloylmethylmercuric acetate, synthesis, 921 heterocyclic bicyclic synthesis, 3621 initiators for electrophilic cyclization of isoprenoids, 2 I75 methoxymercuration of 1, 3-diphenylpropenone, 4709 organ0 - , free radical decomposition, 2281 oxymercurials. confiz. bv NMR. -4321 - Metabolites aureothin, nitro containing, 2701 2-carboxymethyl-3-N-hexyl-maleic acid anhydride, 3519 carotenoids, 25 17. chlorosis-inducing, viridominic acids A and B, 3789 detoxin D, ,2509 la, 25-dihydroxycholecalciferol, active form of vitamin D, , gibl%%, C-9 stereochemistry, 1103 from ent-kaura-2, 16-dien-19. 01, 2723 illudacetalic acid, conversion to illudinine, 2753

Tetrahedron Letters 1972 Metaboiites (continued) isariin, cyclodepsipeptide, 2693 methyl acethydroxamyl acetate, 1195 mucidone, pyrone, 4159 phosphoramidon, microbial - ,97 products of P. herquei, 4729 viridominic acid, steroidal from fungus, 199 Metaliation dichloromethyl-alkoxides, 4 117 regio-specific, lithium di-isopropylamide, 35537 Methylation S-benzylidenebarbituric acid, 5297 dlazomethansd, , 1501 iodo - , Zsubs thiothiazoline, 2743 4-t-butyl thiacyclohexane, 4921 Methyl group detection on C-OH, formylation PMR shift. 4865 Miceiles alkaline hydrolysis of p-nitrophenyl acetate, 4581 cationic, with dichlorocarbene, 1461 influence on speed of SNI and SN2 reactions, 4221 solubilization, effect on counter ion binding, 5 13 Migration aptitudes in thermal[ 1,5] -sigmatropic rearrangements, 5 195 cyanide, 3-benzyl-3-cyanoindazole, 4529 cyclopropyl group, 3249 cyclopropylinethyl groups, cyclohexadienone reactions, 5 17 ferrocenylmethyl group, 3535 kinetic phenyl - , 157 1 methoxyl - to carbenes, 4407 P-naphthalenones, 4391 pyrazoles, [ 1,5] sigmatropic, 937 sigmatropic acyl - ,4533 [ Molecular orbital calculations Del Re, nitro, cyano and iodo group parameters, 2275 diaziridine, 245 1 extended Huckel, bicyclopentane, 3713 naphtho [b] cyclobutene, ion pairing, 2439 Prins reaction, oxetane intermediates, 2797 redox systems, aromaticity, 4835 SCF-MOCNDO, chelotropic reactions, 4347 n4 s + 7? s per&cyclic reactions, 1409 tetrabenzocyclooctatetraene, inversion barrier, 4677 6a_thiathiophthens, 2537

Molecular orbital calculations (continued) mm-l-subs-l, 3-butadienes, CND0/2,3329 o, P-unsaturates oximes. aldehvdes and ketones, CNDO correlations with ‘“c NMR. 565 vinylencarbonatei, cheletropic reactions, 1119 Molecular orbital theory butadiene, photoelectronic spectra, 2739 chemical shifts of substituted methanes, 1453 double bond distortion, 479 Molybdenum compounds carbonyls, alkyne photochem., 1589

Named __. reactions

Arbuzov reaction, halophosphines with aldehvdes. 3953 Bayer-Villiger oxidation, 2669 Cannizzaro, mechanism, 3983 Claissen rearrangement, norbornenes, 2207 Cope ionic rearrangement, ion trapping 891,895 4-methyl-hexa-1, 2-diene-5yne, 3571 Corey oxidation, 315 1 Curtius rearrangement in aminimides, 289 Darzens, synthesis of gylcidic esters, 376 1 vinylogous, 1507 Diels-Alder, anomalous, 2-methyl3-vinylbenzo [ b] thiophene, 4727 bicyclo[2.2.2] octenes, 121 5,6-cycloalkenoo-pyrone, 4691 inverse, pyridazines with aminopropynes, 15 17 thiophene, 605 Friedel Crafts; t-butylation of 2naphthol, 4183 Koch-Haaf, carboxylation. of acyclic+znones, 4707 Koenigs-Knorr, 4053 Meisenheimer transformation, (+)nupharidine, 1503 Michael addition, 3-keto-1,4, 6trienes, 4625 Michael, new reaction, 5023 5027 Michaelis-Arbusov, diethyl phenylphosphonate formation, 31 Nef, conversion of -r-nitroketones to T-diketones, 1331 prostanoic acid synthesis, 3815 photo-Fries rearrangement, kinetics, 1575 Prins, oxetane intermediates, 2797

Subject Index Named Reactions (cortrbrued) 2-pyrone, (+)-occidentalone, 465 I Ramberg-Backlund, 4319 Schmidt, on camphor, 187 Simmons-Smith, improved, 4593 methylenation of As-steroid, 36.55 Stevens rearrangement, naphthalene cyclophaine, 3639 Stobbe, ferrocenes, 5005 von Braun cyanogen bromide, stereochemistry, 355 Wittig, modified, stereoselectivity, 669 Naphthalenes a-aminoacids from, 3 145 3,4-dihydro-3,4, 8-trihydroxy-1 (2H)-naphthalenone, isolation,

Naturally occuring compounds (continued) linarioside. chlorine containinr iridoid glucoside. 4 19 robustic acid. 759 salvigenin, bud excretions, 797 suberine, 1127 surugatoxin, 2545 taondiol, marine alga extract, 2259 tetracyclic diterpenes from rhododendron, 1381 theaflavins from black tea, 463 thymol derivs., 2827 Nitration dimethylphenylsulphonium methyl sulphate, 17 1-methylpyrazole 2-oxide, 2771 1, Ifiimethy 1 - , detritidtion, 2 19 1 Nitrenes intermediate, in nitroso deoxyinter-ring coupling, 179 gendtion, 4059 2, 13-dithia-13.31 (2,7)naphthalphenyl - , ring contraction, 223 1 enophane, Stevens rearrangesulphinyl - -sulphoxide reaction, ment, 3639 5309 highly substituted, 4359 Nit&s 1-hydroxy-l-methyl-l, 2, 3,4-tetraa-allenic, 3257 hydronaphthalene, 4605 amino-acid synthesis from, 1199 methyl naphthalene-2-carboxylate, anhydrous glycolysis, 4643 photodimer, 4721 aromatic, synthesis by metal cyp-naphthalenones, migration, 4391 anide exchange, 4 169 naphtho[b] cyclobutene, 2439 phenylmalode - , condensation uhotodimers from - _321 with diphenylcyclopropenone, Naihthoquinones 3883 2-hydroxy - .4685 succino - , decyanuration, o- and reduced dis - , p-dihydrodiospyrin, fl-dialkylcinnamonitriles, 1003 4201 Naturally occuring compounds p&unsaturated, synthesis, 487 ageratriol, sisquiterpene from Nitro compounds addition to ynamines, 4 1 achillea ageratum, 1397 aromatic nitro group conversion archangelin, revised structure, into donating substituent, 3811 asatone, isolation and structure, 3835 1607 aureothin, metabolite, ‘% NMR, asparagusic acid, plant growth in2701 hibitor, 2549 dinitroalkenes with KCN, slow brugierol and isobrugierol, 203 ElcB elimination, 3511 C, pentacyclic triterpane, 386 1 &methyl+nitrostyrene with bencalophynic acid, coumarin extracts. zene, 2829 2715 nitroaromatic unit of aureotine, cis-jasmone, synthesis, 1233 4875 I, 4-dimethoxy-2-nitro-3, 5, 6-tria-nitroepoxides, photochem., chlorobenzene, 2 11 2689 dl-phyllostine and dlexpoxydon, y-nitroketones, conversion to yregiospecific synthesis, 5 105 diketones, 133 1 Farfunium jauonicum. farfuain A Nitronea configuration, 525’1 _ cycloaddition to arylisothiocyanfuranosesquiterpenes, 1039 ates, 4191 gibberellins, 4299 a-ester-imines and oxaziranes jasminin, synthesis of iridane part, from, 4795 1597 heterocyclic steroidal - , with johnstonol, halogenated epoxide acid chlorides, 4795 from red alga, 195 synthesis, addition of nitro compds jolkinolides A and B, to ynamines, 4 1 laurefucin and acetyllaurefucin, Nitrosamines new bromoalcohol and acetate, chiroptical properties, 779 3

Xix

Nitroao compounds aliphatic, reductive rearrange ment, 1319 deoxygenation, 4059 gem-chloro - , ester exchange during photolysis, 593 nitrosamides, amido radicals from, 1413 o-subs. bicyclic - , rearrangement, 7 7-azabicycloheptyCN-oxyl derivs, 3317 bicycle - ,4287 ESR spectra, 555 phosphorus containing, 4449 2, 2, 3, 3-tetramethylaziridine-loxyl, 119 Nuclear magnetic resonance spectra acyclic alcohols, shift reagent, 5305 alcohols and amines, shift reagent complexes, 435 alkaloidal steroids, 3579 alkene sulphonic acids and chlorides, 4323 2-alkyl-2-adamantanols, 4 103 alkylbenzenealuminium chloride hydrogen chloride complex layer, 5259 1261annulene, 4253 4-arylidene-isoxazoline- and uyrazoline 5-ones, 1147 -_ arylketoimines, 4491 aureothin, nitro merabolite, ‘c, 2701 2-aza-3-oxobicyclo[2.2.0] hex-5 ene, 3563 benzo[b]-1, 4-diazobicyclo[3.2.1] octane, (shift reagent), 2631 6, 7-benzo-4,9-oxido [ 1 l] annulenes, 4 129 benzotb)selenophen and benzo(b)tellurophen, 3 177 bicyclic hexo-pyranoside derivs., ‘T, 4879 o-bisabalolone, sesquiterpene, 1295 1, 2-his-benzenesulphonyl-1, 2diethoxyhydrazhre, temp. dependent. 571 bromobornanes and endoJ-subs 1, 2, 3, 4, 7, 7-hexabromonorborn-2-enes, 3277 calcium complexing, 2473 camphor sulphonamides, 985 cdthanncine, new indole alkaloid, 89 ‘%T,cis and tram ethylene phosphines, 1559 ‘%-polarization during diazonium salt reduction, 25 8 1 charge density distribution in organo-metal sulphides, 5341

xx

Nuclear magnetic resonance spectra (continued) p-chloroethanols, hydroxyl proton multiplicity, 3543 chromones, C-methylated, 1103 chrysanthemyl and presqualene alcohols and esters, 4027 7-c&3-ionol, 3915 computer simulation, fungal extracts, 1105 configurational assignment of quaternary centres, I%, 5 163 cyclic dipeptides, 483 cyclodipeptides, 1437 cycloheptanone ring inversion, 4331 2,4cyclooctadienone system, ring inversion, 5 7 deuterated bicyclopentanes, 3551 deuterium isotope effects induced by shift reagents, 879 dichloroketene-alkene adducts, 1245 dihydro-azines, benzene induced shifts, 1417 5’, 6’-dihydrochalcone, 34 19 2, Sdimethoxy-3,6dimetHyl-phydroquinone and p-benzoquinone, 795 1, 8-dimethylnaphthalene, interring coupling, 179 1. 2dimethyl-2-norbornyl cations, 2447 1, 3-dimethylurea, lsN labelled, BF, and SbCl, adducts, 227 1, 3-dioxopyrimidine dications, 3823 1, I-dioxo-1, 2-thiazetidine, 213 dipivaloylmethylmercuric,acetate, 921 diterpenoid alkaloids, 435 1 elegantine, oxindole alkaloid, 159 2-endo-hydroxymethyl-5-norbornene, shift reagent, 5039 ethylenic phosphines, 145 eucarvone, acid catalysed reaction, 3625 europium induced shifts, time average geometry, 3539 evosine, alkaloidal sesquiterpene, 941 ferrocenes, Y-spin lattice relaxation, 3709 flavones, shift reagents, 4125 formylation shift, Me detection on C-OH, 4865 free radical decomp. of organ0 mercury derivs. of tin, 2281 furanosesquiterpenes, 85 1 haloacetylenes, 4023 2-haloethanols, methylene protons and H-bonding, 3547 halogenocyclohexanones and haiogenodecalones, 277

Tetrahedron Letters 1972 Nuclearmagneticresonance spectra (continued) Hammet-Streitwieser equn., substituted arenes, 681 helicene, structure and configuration by INDOR and NOE, 2731 I-heteroaryl-pyrazole tautomerism, 3937 homotropylium salts, 3665 p-hydroxy-esters, chiral shift reagent, 4233 ikarugamycin, new antibiotic, 1181,118.5 intrinsic LIS parameters, shift reagents, .1345 isoeugenol dimers, 86 1 isopropyl derivs., 342 1 p-lactams, shift reagent, 3599 lanosterol and dihydrolanosterol, 3515 lanthanide induced shifts, graphical method, 4153 theory, 4267 lanthanide shift reagent, adducts, principal magnetic axis, 1095 principal magnetic axis, 3559 lanthanide-+.-chelates of d-3-TFAcamphor, 3297 macrocyclic dehydroannulenones, 3691,369s malonodialdehyde-di-pentadeuteroanil, variable temp., 371 [7] metacyclophanes, 403 p-methylanisole, protonated, 1477 micranthine, bisbenzylisoquinoline alkaloid, 33 morpholines, 40 13 N-aralkyl-pyridinium ions, 3429 N, N’-diisopropyl thioacetamide, 3843 N-substituted acetone hydrazones, temp. dependence, 367 1 I-oxacyclooctan-S-one, conformation by 251 MHz and 63 MHz ‘%Z,3613 oxymercurials, 4327 perchloro-4-methylene-bicyclo13.2.01 hepta-2.6-diene. 2613 aP,‘a-phenyldthyl~mine salts of 0-alkyl alkylphosphonothioic acids, 1531 phenyl nitrene ring contraction, “‘C, 223 1 I-phenylphosphole, 3353 phosphazenes, 4229 poly(methy1 methacrylate), ‘y, 1359 propellanes, variable temp., 2267 prostaglandins, 3265, 3269 quinoline, shift reagent, 4033 ring inversion barriers, benzocycle octatetraene. 665

Nuclear magnetic resonance spectra (continued) rotation barriers in halogen subs. ethanes, 2779 santalin pigments, 120 I sesquiterpene lactone, shift reagent, 621 shift reagents, 3233 nitrogen-phosphorous bidentate ligands, 63 sesquiterpenes, 2617 unexpected temperature effect 673 limonoids, with bifunctional molecules, 1543 silver induced alkene shifts, ‘v, 4291 slow rotation about C-P bonds, 3’P-‘H coupling, 3261 strained alkenes, “c, 4821 substituted methanes, orbital hydridization and chemical shift, 1453 temperature dependence of NMR shifts, 1099 tetrabenzo[5,7] fulvalene, 273 1, 2, 3,4-tetrahydroquinolines, 3357 tetramethylcyclobutene, ‘%, 1031 1035 thiosulphinates containing heterosteric groups, 3907 torsion around Si-N bonds, 505 1 triglycerides, 2533 tri-t-butylcyclopropenyl azide, variable temp., 3293 01,p-unsaturated oximes, aldehydes and ketones, ‘%, 567 Nucleic acids 2’ and 3’-0-trityluridine, 3345 Nucleophilic reactions acylation, carbohydrates, 3945 compounds with interaction electron pairs, 189 cyanide addition to nitriles, 1199 displacement, 1, l-substituted phosphorines, 1045 formate and oxalate, &2 and E2 pathways, 111 glycerolderivs., substitution, 4497 ol-keto-carbonium ions, 256 1 4-methyl-4H_cyclopenta[b] qu,inoline, 3273 N-cyanoaziridine ring opening, 4121 photosubstitution of tluorobenzenes, 685 prostaglandin intermediates, C,, inversion, 3265 substitution, radical mechanism, 613 secondary amines with 2, 4dimethoxy pyrilium salts, 217

xxi

Subject Index

Oxidation (continued) carbohydrates, with ferrate(VI)ion, 4143 cyclic hydrazines, 245 1 4-(l-cvclohexen-1-yl)morpholine. .25%7 4A, 4B_dihydrophenanthrenes, 2853 2,5-di-t-butyl- and 2,3,5-tri-tbutyl-pyrrole, 1337 1, 2-dithiol-3-thiones, 771 oXndiiWOlilleS ferrocenyldihydropyridine with synthesis and fragmentation, 3169 DDQ, 93 oxathiiines a-formyi ketones, 3 115 6-acetamido-5, 6-dihydro-1,4, 2 - , furans, 6-kydroxy-2H-pyran-3(6H)OXathiolpneS ones, 133 I, 3 - , acid ring opening, 2569 hexamethyl, 3133 OxpthiOleS imines, by lead tetraacetate, 19 I, 2-oxathiole-5-one, sulphenoto oxaziridines, 633 carboxylic acid anhydride,deriv., isoeugenol dimers, 861 3689 oxyporphyrins, 2463 OxaZiIleS phenyl sulphides, polarographic, C-hydroxy-1, 2 - , 2861 4513 OxaZilalU?s phosphoramidate, 2553 photochem. of oximes, 115 1 photo - , benzhydrylidene-cycloOxaziridines butane, 3583 oxidation of imines with hydrogen mono and sesquiterpenes, 9 peroxide, 633 photosensitized, silyl enol ethers, oxazolines 2423 arylazirine photocycloaddition, quinone-methide, 1449 4087 sulphides, with l-chlorobenzotri2-benzal-4-phenylpseudooxazoloneazole, 501 5, photodimerization, 3347 tetramethyl-1, 3_cyclobutanedione, 4-beniylidene-5-oxazolones, 2865 concentrated hydrogen peroxide 2-phenyl-2-oxazolin-4-one, 4039 3483 Oxepins tetraphenylhydrazine, radical benzo[b) - ,5203 identification, 5009 2, 3-dihydrobenz - , ring contracthionyl chloride, 4823 tion (DADI), 4503 Oxidative coupling Oxetanes acetylenic heterocycles, 4831 Optical activity &is-l, 2-di - ,4997 intermediates in Prins reaction, abscisic acid, sesquiterpene, 2521 OXiItleS acetoximes with organo-magnesium alcohol synthesis, 4605 2797 aryl methyl sulphilimines, 1377 compds., 1007 photochem of non-conjugated 2, 3-diary1 cyclohexanones, redn., helical conductor model, twistane, dienones, 3679 2251 4355 Oxidation cis-dienone - , thermal cyclization, alcohols, AgCO, mechanism, 4445 Optical rotatory dispersion 313 by cupric oxide, vapour phase, macrolide antibiotics, 5053 nitrosamine acids, chiroptidal 2-furfuraldoxime, catalytic hydro257 genation, 4099 aldehydo 2, 3-dideoxyhex-2-enose effects, 779 photochemistry, 115 1 triacetate, 3 15 1 Organometallics synthesis, addition of nitro compds.. alkenes, KMnO,, improved, 4907 addition to methoxy and carbonyl - . groups, stereochem., 37 to ynamines, 41 thallium triacetate, 347 aromatic nitrile synthesis, 4169 CL&unsaturated. ‘%ZNMR. CNDO ammonia, giving azines, 635 correlati&, 565 ’ percarboxylic acids in presence cadmium compds., asymmetric reactions, 5227 of ketones, 529 Oxindoles copper carboxylates with organyl alkaloids, indole conversion, 1081 anodic, anthracenes, 1449 halides, 49 1 restrained, 965 conversion to aspidosperma skelethoxycarbonylmethyl copper, aromatic hydrocarbons, 2419 eton, 5023,5027 prep. of y, b-unsat. esters, 1163 aromatic N-oxides, electrochemiOxiGUIeS isocyanates, thermolysis, 1065 acid promoted ring opening, nucal, 427 lithium dimethylcopuer, cleophilic participation of 5-benzylidenebarbituric acid, __ 293 magnesium compds. with oximes, methylation, 5297 HMPT, 1209 1007 oxiranyl radical, configurational bisazine, 629 with thioamidc vinylogncs, 3471 stability, 981

Nucleophilic reactions (continued) sulphonium salts, 3879 thiophenes, 402 1 Nucleosides acylvinylphosphonium salts with nucleoside base derivs., 439 adenine 8, 2’-cycle - , synthesis using diphenyl carbonate, 1169 carboxymethyl - ,5349 3Q-D-glucopyranosyl-6-methyluracils, rotational isomerism, 3911 diacetylanhydrouridine, photolysis, 4667 cr-D-methyl glucopyrannoside, 5001 pentopyranine A and C, cytosines with a-L-config., 3991 phosgenation, 4043 phosphorylation, 157 pyrazomycin, antibiotic, 2279 transformation into 5-deoxy derivs, 585 Nucleotides alkyl esters, 2553 8-chloroadenosine and phosphate esters, 2595 9$-D-arabinofuranosyladenine3’, S’cyclic phosphate, 4681 internucleotide bond synthesis, 2881 oligo - , polymer support for synthesis, 1527, 1531, 1535 oligonucleotidic chain synthesis, 3437 synthetic analogues of poly - , 5349

Organometailic~ (continued) metallocenes. rim? basicitv. 269 methyl lithium with 7, ‘I-iibromobicyclo[4.1.0] hept-3-ene, 539 tellurium acetates, 4779 OXUliiines oxidation to oxaziridines, 633 Oxadiazoles 1,2,4-,4959 stereochem., 4191

xxii Ohants (continued) photochemical 1,3_cycloaddition to carbonyl compds, 5133 Oxonium salts 1, 3-dioxolan4one2-ylium and 1, 3-dioxan4one-2-ylium hexachloroantbnonate, 5221 Oxygerution b&l, 2+enzylidenecyclobutane, 4997 terminal alkenes to ketones, 5273 Ozonolysis 6, 7-dimethoxy-exo-tricyclo[ 3.2.1.0’**] oct&me, 4411

. . . eemcdlma

6-and 7-alkyl - ,4917 C-6 (7)~alkyl derivs., and cephalosporins, 375 6-epi - , facile preparation, 285 (-)flavoskyrin, colouring matter from penicillium islandicum, 735 p-lactams and lanthanide induced shifts, 4267 1,2-seco - ,4387 transformation into 2-azetidinones, 5097 Pentalenes benz[b] azapentalenium salts, 953 Peptides activated tosyl - , cyclization, 4283 coupling, chlorotrisdimethylaminophosphonium perchlorate, 4747 cyclic di - , conformation, 483 cyclodepsi - , isariin, 2693 cyclodi - , 1437 cyclopeptide alkaloids, 2609 amphibin A, 865 depsi - , detoxin D, , 2509 electrophoreds, o&o-L-proline, 3795 improved solid phase synthesis, 1581 ketimine derivs of amino acids in synthesis, 2261 new prep. 5047 N-phosphonium salts of pyridines, 415 solid phase synthesis, racemization, 2665 synthetic amides by resin ammonolysis, 101 Peracids oxidation of ammonia by, Peroxides adamantylideneadamantane peroxide, 169 bis - , structure, 3583 diacyl - , thcrmolysis, 4759,4765

Tetrahedron Letters 1972 PlUlleS 2, 13-dithia-[3.3] (I,l)naphthalenophane , Stevens rearrangement, 3639 macrocyclic ethers, 561 [ 7) metacyclophane and 13-bromo deriv., 403 o-cycle - , rearrangement, 4695 [2.2] paracyclophanes, 45 11 quadruple-layered cycle - ,498 1 Phenalenes 7 7Hcyclohepta[cd] phenalen-7one, 3389 SH-cyclopenta( cd] phenalen-Sone, 331 phenalenylidene, 2749 1,6-addition of cycloheptatriene, 5089 Phenanthrenes 4A, 4B_dihydrophenanthrenes, photo-oxidation, 2853 tetra-subs from Tamus communis, 4869 Phenazines phenazine-S-oxide, photoreaction, 3657 Phenolic compounds isoeugenol, free radical dimerization, 4955 resorcinols, alkylation, 945 Phosgene estimation by 4-(4’~nitrobenzyl) pyridine, 27 nucleosides, phosgenation, 4043 Phospha compounds phosphacyclohexadienes, and phosphabenzenes, 4925 phosphacyclooctadiene derivs, 4439 phosphazenes, 4229 tetraphenyl 2,4,4,6-phospha4-pyridine, 4363 Phosphine-s cis and trans ethylene - , ‘T NMR, 1559 esters, O-alkylation, 829, 835, 839,843 of enynols and allenols, 4933 ethylenic - , NMR, 145 halo - , reaction with aldehydes, 3953 N-(dimethoxyphosphinothioyl) carbamate esters, oxidative rearrangement, 4245 trisdimethylamino - , 5001 tris(tripheny1 - )-rhodium chloride, 4375 Phenols acetamide interaction, IR, 4457 chloro - , hindered, antioxidant, 3743 dicnone isomerization, 1341.4929 lead tetrakistrifluoroacetate with aromatics, 5369

Phenols (continued) 2-naphthol, t-butylation, 4183 perfluoropiperidine with, 5 169 Phoapbinic acid derivs or-halophosphinates, rearrangements, 925 Phoaphites methyl - , with diphenylcyclobutenedione, 787 trialkyl - , nit&so deoxygenation, 4059 triethyl - , reaction with diphenyliodonium salts, 3 1 reaction with ethyl a, @-unsaturated p-nitrocarboxylates, 3995 Phospholes 4, S-dihydro-1, 3, S-oxazaphospholene, photochem. cycle+ . elimination, 1263 1,2-oxaphosph(V)olen, 1421 1, 2, S-oxazaphospholines, 3995 phospholanes, 4209 I-phenylphosphole, NMR, 3353 phospholecarboxylic ester, synthesis, 299 phospholene oxides, 299 Phosphor& acid and derivs 4-acylaminouhosuhonates. 4487 cyciodephoiphonation, 4911 dimethylphosphono- and diphenylphosphinyldiazomethane, 3979 alkylation, 3799 a-phenylamine salts of 0-alkyl alkylphosphonothioic acids, “P NMR, 1539 Phosphonium salts acylvinyl - , reaction with nuclecside bases, 439 alkyloxy - ,500l @-carboethoxy - ,825 chlorotrisdimethylaminophosphonium perchlorate, peptide coupling, 4747 dibenzocyclononatetraene pho.+ phonium ylide, 3361 E-propenyl - , stereospecific formation, 1421 N-phosphonium salts of pyridines, 415,5047 triphenylphosphonium isopropylide, 3781 Phosphoranes imino - ,2635 phenyltetrafluoro - , fluorination of alcohols, 847 Phosphoric acid derivs phosphate enols, 4469,4473 Phosphorins I-alkoxy-l-acetoxy-2, 4, 6-triphenylphosphorine, 1045 cis. trans4methyl-2-oxo-2H-1. 3, 2-dioxaphosphorinancs, iso. merisation, 309

Subject Index Photochemistry (continued) Phosphorins (continued) desoxybenzoins, 3411 heterophosphorines, 829, 835, diacetylanhydrouridine, 4667 839,843 diary1 1,2_dithiolylium salts, 5213 2-0x0- and 2-thiodioxaphosphoridiaryliodonium salts, 4793 nanes, 1485 dibenzothiophen, reduced, re oxyphosphirane intermediates, arrangement, 255 925 4.5~diivdro-1.3.5-oxazaphog Phosphorus compounds phoienes, cycioeliminaiion, carbon phosphorus medium 1263 rings, 5 18 1 4A, 4Bdihydrophenanthrenes. ligands as co-dimer catalyst, 4775 nitrogen-phosphorous bidentate 2853 2, ‘I-dimethylacridine l@oxide, ligands, NMR shift reagent, 63 971,977 nitroxide free radical, 4449 l,2-dimethylenescyclohexanes, pentacovalent P, epimerization electrocyclic reactions, 367 kinetics, 4367 1,2-dioxolanes, 1357 phosphodiester linkages, 2553 3,4-diphenyl-benzocyclobutene, trivalent phosphorous derivs. with 547 or-allenic ketones, 149 diphenyliodonium salts, 3739 Phosphorylation diphenylmalodinitrile, cyclization, alcohols, phosphochloridodithioate, 411 821 1, 3-diphenylpropene-24, 115 1 nucleosides, 15 I 2, 5-de-t-butyl- and 2,3,5-t&tPhotochemistry butyl-pyrrole, oxidation, 1337 adducts from o-chloranil, 175 enamino ketones, 25 13 o-alkoxycyclohexanones, 2415 gem-chloronitrosocompounds, alkynes, metal carbonys, 1589 aminated 1,4-benzoquinone, 593 grayanotoxic skeleton synthesis, 2253 anti-7,8-benzotricyclo [4.2.2.OJ’5 ] 657 deca-3,7,9-triene, 3785 gurjunene, oxidative, 9 azobenzene, cyclodehydrogenation, p-hydroxy-y-pyrone, 4655 indolenin-l-oxide, 3 2 15 2493 keto-ketene generation, 3443 2, benzaWphenylpseudooxazolmethanol and ethanol irradiation, one5,3341 benzhydrylidene-cyclobutane, 1331 4-methoxy cholest+ene-3-one, 3583 benzocyclobutenedione, 5321 2161 2-methyl-2,4-hexadiene, acetone benzocyclobutenone, 3917 cycloaddition, 1229 benzoin ethers, 4755 N-alkoxyisosulphobenzimides, benzonorcaradienes, 117 1 benzophenone reduction, 4949 3289 benzophenone triplets with norN-aroyldiphenylketimines, rebomadiene and quadricyclene, duction, 1053 a-nitroepoxides, 2689 5345 N-nitroso and N-chloroamides, 1-benzothiepine, 4597 bicyclo[4.2.1] nona-2,4, ‘I-trien531 nucleophilic substitution of fluorog-one, 1049 his-2, 3-diphenylcyclopropene anh benzenes, 685 anhydrides, 1579 oximes, 115 1 carotenoids, 25 17 peroxyvalerolactone, 3483 phenazine-S-oxide, 3657 chloranif in alcohols, 3 125 phenylbromopropanes, 1571 cis-verbanone in MeOH, 4573 1-phenylcyclohexene in 2-procychzation of cis, cis- and trans. trans-cyclodica-1, 6-diene, 569 panol, 2663 cycloaddition of benzophenone 1-phenyl-2, 2-dimethoxy-Z(Nto a conjugated enyne, 2265 alkoxycarbonylamino)-diazoethanes, 2469 1, 3cycloaddition of carbonyl compds., with oxiranes, 5 133 photobromination of n-butyl 2,4cyclohexadienone, Dielsbromide with =Br, 3 17 Alder dimers, 5 177 photodimers from dimethyl naphvalence isomerism, 2735 thalene- 1, 8-dicarboxylate and methyl naphthalene2carboxy2,4-cyclooctadiehe, 1349 cyclopentadienone dimers, 303 late, 321

...

xxm

Photochemistry (continued) photo-Fries rearrangement, 1575 photolysis, Nacylindolines, 5031 phthalimide system, 45 17 6,6’-polymethylenebis(4-methyl2-pyrone), 2247 2-pyridone, 3563 rearrangement of steroidal nitrite, 661 reduction of alkylcyclohexanones by propan-2-o1,6 3 7 retro+onones, non conjugated dienones, 3679 selenoketene, 1,2,3-selenadiazoles, 445 silyl enol ether, oxidation, 2423 spire-epoxy-2,4-cyclohexadienones, 4205 steroidal enone -, CD application, 1061 &styryl sulphoxide, 2895 sulphonamide 1, 3-dienes, 3321 1,2,3,4tetraphenylcyclobutane, 551 thienel, l-dioxide, 4781 thiophenes, model for induced valence bond isomerizations, 1429 thymine : 3,4-benzopyrine product, structure, 589 trialkylboranes with fl-dicarbonyl compds., 1167 tricyclo[5.3.0.0s~4]deol-ene system, 3555 p, r-unsaturated ketones, double rearrangement, 677 free rotor effect, 1367 Photoelectronic spectra adamantane and l-bromoadamantane, 5285 butadiene, subs., 2739 1,6-methanocyclodecapentaene, 4107 pentatomic saturated heterocycles, 3853 pyrene and coronene, 2511 trans-15, 16-dimethyl-dihydropyrine, 575 o, p-unsaturated esters, 4271 Phthalazines phthalanylidene ammonium salt, 2711 Phytotoxic substances pyriculol, rice blast cause, 13 PigGents (-) flavoskyrin, from penicillium island&m, 735 _ fungus, grevilline, 4895 santalin A, 3503 santalin permethyl ether, 1201 theaflavins from black tea, 463 Piperidines o-benzyl - , synthesis, 1567 functionally substituted, 1425

Tetrahedron Pip&dines (continued) N-formylation, reaction with RhC4 in ethanol, 173 3-oxotropanium salts, equilibration, 1525 perfluoro - , with phenols, mechanism, 5169 0. Polatograehy nitrobenzene reduction, i835 phenyl sulphides, anodic oxidation, 4.513 PoIycyclic compounds 8-acetoxy&(2,4-dimethoxy-5bromophenyl)-3-methyltri~y~l0[5.2.1.0~‘~] decan-2-one, 5059 alkanes, conformation, 2525 anti-7, 8-benzotricyclo[4.2.2.0”5] deca-3,7,9-triene, 3785 bullvalene, new synthesis, 2589 dibenzo-(CH),,-hydrocarbons, 2573 6, 7-dimethoxy-exe-tricyclo[ 3.2.1.0”‘] octdene, ozonolysis, 4411 endo-&tricyclo[ 3.2.1 .O”‘] octanone, 4095 endo-tricyclo[3.2.1.0’>*] octd-ene, 4577 exo-(CH,>l, 2, 3,4,5,6-hexamethyl-tricycle [ 2.2.0.0Z’6 ] hexane, 4733 exe-tetracyclo[ 3.3.0.03’6.01’s] oct4-yl tolylate, 2289 heterocirculenes, 763 monodechloroaldrin and monodechloroisodrin, rearrangements, 1311 norbornadiene hydrogenation products, 2503 norbornyl endo A* -1, 2, 3-triazoline, 2819 pentacyclo[6.5.0.0”4.03~‘.0’0”J] trideca-5, 11-diene, 4537 1, 2,4, 5,6-pentamethyl-3-methylenetricyclo[ 2.2.0.0ZT6]hexane, reactivity to acids, 5361 phenalenium system, 331 pyrene and coronene, photoelectronic spectra, 25 77 quadricyclene, [6+2+2] cycloaddition to tropone, 39.5, 399 quadricyclo[8.2.1 3*s.0*‘9] tetradeca4, 6, 1 I-tricn-l4-one, 395,399 santalin A, pigment, 3503 tricyclic hexamethyldewarbenzene, 5357.5361 tricyclo[5.3.0.0”6 1decane, 569 tricyclo(3.3.1.13”]dec-I-cne, 4049 tricyclo/5.3.0.0”4] dcc-I-cne, 3555 tctracyclo[4.3.1 .03” .07’91dec4-en2-yl system, 4 17 1 tricyclo]4.4.1.1”“] dodecane, 4887

Polycyclic compound8 (continued) tricyclo[3.1.1.0*“] hept-2-ene, 539 tricyclo[ 3. l.O.OzV’]hexane, kmetics of isomerization, 3757 tricyclohexanes, cyclopropene dimerization, 231 Polyenes 1,5,9-cyclododecatrienes, boron promoted epoxidation, 5093 hexatrienones, diazomethane cycloaddition, 4803 linear non-planar - , chiroptical properties, 597 tetrabenzocyclooctatetraene, ring inversion, 4 187 1, 2, 7-trienes, 4465 Polymerization stereoregular, poly(methy1 methacrylate), 1359 trimerization of conjugated acetyenes, catalysis, 61 Polymers insoluble polymeric carbodiimide, 3281 methyl methacrylate, ‘%ZNMR. 1359 oligonucleotide synthesis, support, 1527.1531, 1535 poly(3,4-diethylstyrene)sulphonyl chloride, 2881 vanillin containing, 5077 Porphyrins dipyrrylmethane and tripyrane, 2203 meso-tetraphenylporphine, carbene addition, 1011 oxophlorin, 2463 phospha - , configurations, 1111, 1115 rhodium complex, 1077 Prenylation nuclear, 3-phenyl-4, 5, Il-trihydroxycoumarins, 759 polyhydroxyketones, 3371 Propellanes free radical, 325 2, 5, 7, 10, 11, 14-hexaoxa[4.4.4] propellane, 2267 14.4.41 propellane synthesis, 137 Pzostaglandins analog synthesis by 1,4-additions, 2627 9, 1 I-bis-desoxy-prostaglandin, 1123 11, 15-bisdeoxyprostaglandins E, , E,, and F,,, 4083 his-homo - , synthesis, 5151 coral, allylic rearrangements, 4346 (+_)-9-deoxy-13, 14-dihydro - , 3341 (t)-1 I-deoxyprostaglandins, synthesis, 773 1 1-desoxyprostaglandins, 2435 synthesis, I15

Letters 1972

Prostaglandins (continucd) 8, 12-diiso-PGE, and dl-PG, series, 4303,4307 (+)-1 I-epi-PGF,o and (-)-I l-epiPGE,, 3269 methyl 9-oxoprostanoate, 1287 new synthesis, 53 17 nocleophilic inversion at C,, of intermediates, 3265 prostaglandine A,, total synthesis, 1491 prostanoic acid synthesis, 38 15 stereospecifec synthesis of prostaglandin F,o, 3333, 3337 synthesis, route to intermediate, 107 Protecting groups p-aminoalcohols, 4867 o-benzyl, tyrosine, 3475 Proteins collagen models, oligo-l-proline, 3795 Rotonation amides, 2485 5-azaindoles, 2857 p-methylanisole, 1479 polyprotonated species, 4929 rates and basis&y, N, N-dimethylpropargylamine, 521 ring - , benzidine rearrangement, 2707 Ptezidines fragmentation mechanism, 3219 synthesis, 3359 Purines 7-deaza - , 2301 pVran.s aminodihydropyranes, 4663 dihydropyran-2,5-diones, 4895 2-ethyl-2-amino4-desoxy-O-(pD-glucuronopyranosyl)a, pD-glucopyranoside, 43 1 6-p-methoxyphenyl-3-p-methoxythiobenzyl-2, 3-dihydro4Hthiopyrannes, 347 1 2, 3-unsaturated methyl pyranoside, reductive rearrangement, 1205 Pymzines 2amino - , bioluminescent jellyfish, 2747 cyan0 - , cyclization, 4771 Pyrazoles annelated, gas phase pyrolysis, 2235 benzo-di - and tri - , 1593 I-heteroaryl - , 5-hydroxy tautomer, 3937 I-methylpyrazole 2-oxide, nitration, 2771 Nacyl -- ,4533 pyrazolo-ehromones, 1593 spontaneous [ 1,5] sigmatropic migrations, 937

Subject Index Pyrazoles (continued) Pyrimldimd (cofltinued) 3,4,5-triphenyl,4979 benzo (1) thieno[ 2,3-d] - and b Pyrazolines benzo (1) thieno[ 3,2-d] - , 4-arylidenspyrazoline-5-ones, 4549 NMR, 1147 5-benzylidenebarbituric acid, oxiPyzenes dative methylation, 5297 3,4-benzopyrene : thymine photo brommation, gas phase, 2183 product, 589 4,5-dihydrofuro[2,3-d] pyrimidtrans-15, 16dimethyl_dihydropyines, 3457 rene, photoelectron spectrum, isomeric dihydro - , NMR, 1417 575 thymidines, gamma irradiation, Pyridazmes 3225,3229 hydrazine with methylenecyclouracil dication, 3823 propene, 3731 Pyrolysis methoxycarbonyl - , with diethylannelated pyrazoles, 2235 aminopropyne, 15 17 arenylphosphonic acids, cyclization, 4,5,9, lO-tetraazapyrene add N4977 oxides, 3643 benzocyclobutenone, 39 17 s-triazolo(2, 3-bj - ,4179 cY-benzoxylactones, 3375 PyIidines his-2, 3-diphenylcyclopropene an4-alkyl- , synthesis from 4-( lH)hydrides, 1579 pyridones, 1237 2-chloro-1-methoxyethyl acetate amino - , ionization potentials, and thiolacetate, 5159 3193 diazirine, 4347 azaphospholo-dihydropyridine, homophthalic anhydride, 1249 4229 methyl-[ 3.2.01 bicyclohept-ZenI-benzyl-1,4_dihydronicotinamide, ‘I-ones, 5 19 1 4883 ochotensine isoquinoline alkaloid, 4-(4’-dinitrobenzy)pyridine with 4847 phosgene, 27 peroxides, 4759,4765 diphenylbutadiyne benzylamine peroxyvalerolactone, 3483 synthesis, 3487 sulphoxylates, 3121 ferrocenyldihydropyridine, oxiPyron& dation with DDQ, 93 5, 6-cycloalkeno-ol-pyrone, 4691 5H-2, 3-benzpyrano[ 4,5-b] pyri2, 6-diethyl-diaminw - , 1131 dine, 1445 3, 6-disubstituted-2-pyrone, muciisomeric dihydro - , NMR, 1417 done, 4159 N-oxide with Grignard reagents, phydroxyy-pyrone, 4655 311 2-pyrone, Diels-Alder reaction, N-phosphonium salts, 415 4651 peptide synthesis, 5047 PyrrOk? phenyl - and thienyl - , basisity, cycloaddition, 4703 233 2,5-dihydro-2,4-disubs - ,407 1 pepidone ring, nucleophilic addition diphenylbutadiyne benzyhmine elimination. 5 109 synthesis, 3487 pyridones, protomeric equilibria, dipyrrylmethane and tripyrrane, ??C #,.I 2203 tetraphenyl2,4,4,6-phospha-4imidazole-Ac, Q-reagents and, pyridine, 4363 4723 Pyridmium salts photooxidation, 1337 isoxazolo[ 2,3-a] pyridinium salt ring cleavage, ‘I-deazapurines, 2301 rearrangement, 609 synthesis, Michael acceptors and N-aralkyl-pyridinium ions, 3429 tosylmethylisocyanides, 5337 N-(2-cyanomethyltryptophyl) tetrapyrrole metal complexes, 3803 pyridinium tosylates. 2639 trichloroacetyl isocyanate and, N-methyl+(chrysanthemyloxy) NMR, 5167 pyridinium iodide, solvolysis, pvnolidines 67 1, 2-disubstituted, quaternization, N-vinyliminopyridinium ylides, 4233 with alkynes, 5245 steroidal alkaloid photochem., Pyfylium salts 5015 2,4-dimethoxy - , action of vinylpyrrolidones, 4695 secondary amines, 217 Pyrrolines Pycimidines arylazirines, photocycloaddition, 2-alkylamino-5-(2-hydroxyethyl)4087 pyrimidonc, 3457

xxv Pyuolinea (continued) pyrrolinones, Rugglt synthesis, 2787

Quateanary s&a ammonium ions, dealkylation, 2167 1,2_disubstituted pyrrolidines, 4231 hindered amines, 3857 stereochemistry of elimination, 3439 Quinolin~ I-alkyl-1 ,4-dihydro - , ring expansion, 4863 4-methyl-4Hcyclopenta [b] quinoline, 3273 NMR in presence of shift reagents. 4033 1,2, 3,4-tetrahydro - , optical purity, 3357 UV spectra, 1555 Quinoloned quinolone-(2)-alkaloids, new, 449 Quinones ammated 1, Qbenzo - , photo them, 2253 antibacterial, 795 chloranil, photochem, 3 125 difurobenzo - , cyperaquinone and conicaquinone, 241 diquinucyclobutene, 145 1 methide, oxidation, 1449 santalin A, pigment, 3503 o-naphthaquinone, 4 183 p-benzoquinone with cysteme ethyl ester, reinvestigation, 1327 3, 5, 3’, 5’-tetra-t-butylstilbene 4,4’-quinone, 4219

Racemization aryl methyl sulphilimines, 1377 solid phase peptide synthesis, 2665 thermal, helicenes, 3707 Rearzangements abietic type resin acids. 4947 aliphatic nitroso compds.. 13 19 arylhydrazonates to N’. N’-diarylhydrazides, 3211 1,4_arylradical - , 1567 azasulphonium salts, base catalysed, 497 backbone, hyperacids, 4739 benzidine, cation radical mechanism, 3675 ring protonation, 2707 benzonorcaradienes, photochemical 1171

xxvii

Subject Index Selenium compounds benzo(b)selenophen, NMR, 3177 selenadiazoles, polarography, 3835 selenanes, axial preferences, 4335 selenol and denon esters, 375 I Sex attractants (-)-methyl n-tetradeca-rruns-2, 4, $$noate, dried bean beetle,

Solvolysis (continued)

N-bromoamines, 875 N-methyl4(chrysanthemyloxy) pyridinium iodide, 67 sulphonylmethylperchlorates, 617 4-tosyloxytwistanes, 699 Spiro compounds 6-methylspiro[4.4] nonan-l-one, CD, 883 oxaspiropentanes, 887 scsquiterpenes, stereochem., 899 Silicon compounds amino-silanes, torsion barriers, spiro[adamantane-2, 2’-adamantane], 1175,1179 5051 9, 9-dimethyl-9H-tribenzo[b,d,f] spiro[4.5] deca-I, 4-diene-3-tarsilepin, 4669 boxylate, 2495 dimethylsilacyclobutanes, 3495 spirorepoxy-2,4-cyclohexadiensilacyclobutanes, 525 ones, 4205 spiro[2,4] hepta-4,6-diene, 3531 Silylation alcohols and amines, 525 Spiro hexan-rl-one, 4593 Singlet state Spiro-2, 3-hex-rlenes, 1371 oxygen addn. to silyl enol ethers, Spiro-norcaradiene, 1255, 1259 spiropyrazolines, 3479 2423 singlet oxygen chemistry, 45,49 swazine, dilactone alkaloid, 707 role of azide 1, 1, 2-trisubstituted spiro[2,5] Solvent effects octanes, 2255 anchimeric assistance, glycol mono- Staeochemistry benzoate solvolysis, 4617 alaskenes and acorone related diarylamidines, hindered rotation, sesquiterpenes, 899 antheridiol, fungal sex hormone, 5281 3-diazo-2norbornanones, 1069,[ 791,2673 bimolecular elimination, base ion1073 acid catalyzed decomp., Q, P-epoxyketones, with HCl and pairing, 23 calamenes, sesquiterpenes, 905 HBr, 783 heterocyclic alkynes, oxidative carbene addition to meso-tetraphenylporphine, 1011 coupling, 4831 iodo lactones of bicyclo[2.2.1] chiral phosphorus thioacids, 1539 chrysanthemyl and presqualene heptane with hydroxide ion, alcohols and esters, 4027 1143 cyclopropane ring opening, 4095 o-nitroepoxides, photochem., 2689 oximes, cyclization versus elimidimethy ketene addn. to 1, 3dimethvl aflene. 2499 nation, 1213, 1217 I? s + n’s cycloadditions, .+tetradynamic i, Si-N bond torsion, zones, 1401,1405,1409 5051 troponoid-maleic anhydride cycloenamine formation, 3607 addition, 2685 o-epoxy-ketone red”, 4371 water on solvolysis of sulphonyleffects, sesquiterpene alkaloid, methylperchlorates, 6 17 941 Solvolysis gibbanes, C-9 assignment, 1103 cyclopropyl group, 4799 glycidic esters with trimethylalu7, 7-dibromobicyclo[4.1.0] hep minium, 1001 tane, 4427 hexamethyl reactions, 3137, 3 141 exo-bicyclo[ 2.1.01 pentyltosylate, 3p-hydroxy-4,4-dialkyl-Sa-ster359 oids, 460 1 exo-tetracyclo[3.3.0.0”‘6.0a*s] octikarugamycin, antibiotic, 2557 4-yl tosylate, 2289 isolongifolene alcohols, 3865 fluoroalcohol - , t-butyl chloride ketene : imine cycloaddition, and 7-methyl-7-norbornyl 3633 tosylate, 3617 mechanisms of catalytic hydra heteroarylmethyl derive., substitgenation, 5155 uent effects, 3889, 3893 3-methylenecepham derivs., 3241, holarrhenine mesylate, steroidal 3245 alkaloid, 1305 noncoplanar double bonds, 475 3P-hydroxy.-4,4-dialkyl-So-steroids o-xylylene cycloaddition, 2443 and p-toluene sulphonates, 4601 phosphaporphyrins, 1 I1 1, I1 15

Stereochemistry (continued) prostagbmdin synthesis, 2627 quaternary ammonium salt eliminations, 3439 saturated ‘flat’ carbon, 43 15 steric control in reduction of achiral ketones, 687 7-substituted norcaradieneq 345 1 sulphinyhritrene-sulphoxide reaction, 5309 sulphoxides, 4839 4-t-butyl thiacyclohexane methylation, 4921 von Braun cyanogen bromide, 355 Stereospecificity o-amino-acid synthesis, 2565 cis-@-lactam synthesis, 2823 1, 2-dialkyl-3_carbomethoxycyclopropenes, ring opening, 3367 1, 3-diene telomerization, 4009 ferrocenes, 2885 photocycloaddition of acetone and 2-methyl-2,4-hexadiene, 1229 photoreduction of alkylcyclohexanones by propan-2-o& 637 protonation, l-methoxyhomotropylium cation, 4399 tetrahydrocannabinol synthesis, 2507 Stezic effects addition of unsaturated organometallics to methoxy and carbonyl groups, 37 disiamyl borane addition to 2alkyl propenes, 245 esterification, carboxylic acids, 757 hindered carboxylic acids, 4063 free radical addn. of thiols to norbornenes, 2719 inhibition of conjugation, 909, 913 requirements of leaving group, 2465 rotation barriers, halogen effects, 2779 t-butyl cyclobutadiene and cyclopentadienone, 1025 3-t-butylcyclohexene, electrophilic attack, 3527 Steroids alkaloidal, conanine, 505 deuteration of 19-Me, 3499 photochem., 5015 antheridiol, fungal sex hormone, 791,2673 2-aza - , 3237 azido - and amino - , C-5 epimers, 3579 B-homo-A, 19-bisnorandrosta-5 (lO)ene-3, 17dione, 248 1 5a-cholesta-9(1 l), 17(20), 24-triene3p,6a-diol, star fish genin, 3721

...

Tetrahedron Letters 1972

xxv111

Steroids(continued) deacetylation and acyl migration, 3349 19(29)-dehydroursolic acid, 1515 3p, 12a-diacetoxyd’4”6-Sa-pregnadien-20-one, reduction, 3415 dienones, o-methylation, 961 3&6cr-dihydroxy-5o-pregn-9(1 l)en-20-one, 5263 D, L-androstenediones, total synthesis, 96 1 ene-diols and triols, 4501 enone photochemistry, CD measurements, 1061 4p, Sp-epoxy-3-ones, 783 glycocynanchogenin, a polyoxypregnane, 4005 holarrhenine, solvolysis and rearrangement, 1305 lar-hydroxy and 25-hydroxy - , 4147 3fi-hydroxy-4,4-dialkyl-5o - , stereochem., 4601 3a-isopropyl-3, Sp-epoxy-A-norcholestane with BF, , 7 17 3-keto-1,4, 6-trienes. Michael reaction geometry, 4625 lanosterol and dihydrolanosterol, NMR, 3515 As - , methylenation, 3655 new sterol from asterosaponins A and B, 1601 nitrones with acid chlorides, 4795 19-nor-5-methyl-5p-cholestane, 2877 pregnane derivs., 4795 ring B cleavage in 513- ,261 3,4-seco-3-nor-friedelan-2-al, 3397 taondiol, marine alga extract, 2259 3p, 6o 23f-trihydroxy-5a-cholcst9(1 l)-en, 3725 (x,/3-unsaturated ketone redn., mechanism, 4673 viridominic acid, fungus metabolite, 199 strain alkenes, ‘YJ NMR, 482 I bicyclic allene, 287 1 cyclic betaines, 2603 torsional, noncoplanar double bonds, 475 Substituent effects benzcnc reactivity, 3203 bicy3c:;l;entane isomerizations, 1, I-bishomocubane rearrangemcnt, 4913 diarylamidincs, hindered rotation, 5281 3-diazo-2-norbornanoncs, decomposition. 1073

Substituent effects (continued) free energy plots, linearity deviations, 753 heteroarylmethyl derivs, solvolys sis, 3889,3893 hydroxy group in photochemical rearrangements, 3785 spectral and reactivity data using Hammett, 5 187 o, p-unsaturated esters, 4271 Substitution reactions aldehydes of heteroaromatic bases, 4 113 o-chloro-o, o-diphenylacetamide with potassium phenylcyanide, 805 nucleophilic photo - , fluorobenzenes, 685 1-phenyl-cyclobut-I-ene-3,4dione, 3885 o-sulphonyl carbon, 2477 Sulphiies benzyl - , with (n,n*) triplet ketones, 3925 p-hydroxyalkyl phenyl - ,737 organo-metal - , ‘%?NMR, 5341 oxidation with l-chlorobenzotriazole, 501 phenyl - , anodic oxidation, 45 13 synthesis from thiol esters, 379 o!,p-unsaturated - ,47 13 Sulphilimines and sulphoximines, 4137 aryl methyl, thermal racemization, 1377 ‘free’, preparation, 16 19 Sulphlmes acyclic o-sulphinyl carbanions, 4839 alkylsulphinyl and alkylsulphonyl radicals, ESR, 4075 aromatic, diazomethane addn., 2293 aryl-sulphine bond, restricted rotation, 5329 sulphenylphosphinimine and sulphenylsulphoximine, 3405 sulphinylnitrene-sulphoxide reaction, stereochem., 5309 sulphinyl transfer reagents, 53 13 Sulphonic acid derivatives alkenesulphonic acids and chlorides, 43 19, 4323 arenesulphonates, p-elimination, 2621 diacylglycerosulphonates with carboxylate ions, 4497 sulphonamides, camphor, 985 hydroxybenze, 25 1 t-alkane, synthesis, 18 1 a-sulphonyl carbon, intermolecular substitution, 2477 vicinal di-methanesulphonated, conversion to alkenes, 3447

Sulphonea cyclic, cathodic cleavage, I469 Sulphonium salts amino- and alkoxy - ,501 aza - ,497 betaines, decomp. to epoxides, 3313 dimethyl-hydroxyphenyl - , 3879 dimethylphenylsulphonium methyl sulphate, nitration, 17 diphenylsulphonium cyclopropylide, 887 imidodialkvl - .625 &ketosulphonium halide-copper halide complexes, 407 Sulphoxides p-hydroxy - , alkenes from, 649 p-keto - , cyclization, 3393 methyl methylthiomethyl - , 2681 phenylacetic acid synthesis, 1383 sulphoxylates, pyrolysis, 3121 Sulphur compounds heterocycles, electronic structure, 4165 elemental sulphur with haloaromatics, 1283 iminosulphurane synthesis, 2635

Tautomexism aldehydoacid-lactol, 2753 ethylacetoacetate, UV influence on, 4017 I-heteroaryl-pyrazoles, iminoether-enamine, 2459 Tellurium compounds organotellurium acetates, 4779 Telomexization stereoselective, 1, 3-diene, 4009 Terpenoid compounds 1-abietic acid, hydrofluorene from, 4509 abscisic acid, optical activity, 2521 ageratriol, sesqui - , 1397 alaskenes and acorone related sesqui - , stereochem., 899 CXand p-pinene, chlorosulphonyl isocyanate addn., 495 1 antibiotic LL-Z127 lo, synthesis, 695 (+>arbusculin B, 3375 ascofuranone, fungal - , 254 1 axivalin, lactone, 4423 baccharane derivatives, 5043 o-bisbalolone, new sesqui - , 1295 calamenes, cycloalkene aromatization, 903,905 cedrene, biogenesis, 2455 components of boll weevil sex attractant, 669

Subject Index Thermochemistry (continued) Terpenoid compounds (confinued) bicyclo[ 4.2. l] nona-2,4, ‘I-trienconfertolide, scsquiterpene lactone, 9-one, 1049 207 . . &carboethoxyphosphonium salts, C,, pentacychc trlterpane m 825 messel oil shale, 3861 cis-dienone-oximes, 3 13 cyclizacorollatadiol, tri - , 4525 elemol conversion to eudesmols, tion, condensation of silylated ketene 5139 acetals with aromatic aldehydes, epoxyfarnesol and farnesol, 2, 379 double bond isomerization, cycloaddition, tropone with 5101 dimethyl quadricyclene-2, 33cr, 4&epoxyshionane BlZ3-St20 catalysed rearrangement, 5043 dicarboxylate, 399 evozine, alkaloidal, 94 1 cyclohexadienones, cyclopropyl(-)-frullanolide, 2489 methyl migration, 5 17 cY-elimination of acetic acid from fungal extracts, NMR simulation, methyl acetate derivs, 3623 1105 furanosesquiterpenes, new, 1039 exoJ-subs bicycle [ 2.1 .O] pentanes, NMR 851 355 1 futronolide, drimane type sesqui flash thermolysis, ketoketenes, - ,4257 3703 gurjunene, photooxidation, 9 helicene racemization, 3707 inumakilactone E, plant growth homo[ 1.51, [1.7)shifts, 125 inhibitor, 3385 5-methylene-bicyclo[ 2.2.11 heptisolongifolene alcohol stereochem2-ene, 3465 istry, 3865 organometallic isocyanates, 1065 jolkinolides A and B, 1387 2-0x0- and 2-thiodioxaphosphorileucothol B and D, configuration, nanes with boron trifluoride, 3831 1485 longibornane system, fragmentation, selenoketenes, 445 thermolysis of elemol, 5 139 715 mono - , cyclization, 2431 6-unsaturated-ketones, 4461 head to tail biosynthesis, 67, Thermodynamics 71 diastereometic product ratios, new from Sideritis leucantha and 5293 Sideritis linearifolia, 2 187 hexamethyldewarbenzene, pronordi - , 3385 tonation, 3197 pachysandiol-B and pachysonol, protomeric equilibria, pyridones, 5249 775 photochemical synthesis of grayThis compounds anotoxins, 657 4-t-butyl thiacyclohexane methyreduction, (Y,&unsat carbonyl lation, 4921 compds., 5035 2, 13-dithia-[3.3] (2,7)naphthalretigeranic acid, sester - (4609 enophane, 3639 santalene, copacamphor and ylandithians, sulphonium salts and gocamphor, synthesis, 3683 sulphoniumylids, 989 p-santalene, synthetic approach, 6a_thiathiophthens, CNDO, 2537 2207 Thiazenium salts sesquiterpenes, lactone, NMR, l,3-,3977 621 Wetidies synthesis, nootkatone, 2617 1, 1-dioxo-1,2- - ,213 synthetic intermediate approach, Thiaziies 3987 2, 2’-bi(ZH-I, 4-benzothiazine), tetracyclic di - . rhododendron 1327 extracts. 1381 dihydro - , ring closure to, 5301 Tetrazines 1,4 - , reductive cleavage, 5 199 cycloaddition of, 4295 Thiaz&s hexahydro-1,2, 3,4- - ,949 2,4-dithiazoles, 15 13 Thallium compounds synthesis, 2777 triacetate, oxidation of alkenes, 2, 3,4-trimethyl thiazolium brd 347 mide, 265 1 Thermochemistry aryl methyl sulphilimines, racimiThbZOlidineS zation, 1377 2(2, 6-dimethyl-phenyl)-imine azasuluhonium SdtS. 497 (2-chlorobenzoyl)-thiazolidine, 3179 azo cimpds., 387

xxix Thkzolines 2-arylamino-2-thiazolines. 152 1 arylazirine photocycloaddition, 4087 2-methy- - , aldehydes from, 3929 __-_ Zsubstituted thio - , 2743 ~hiepin 2,3- and 2,7-dihydro - ,3119 1-benzo - . Dhotochem.. 4597 Thiirrnes ‘iodine thiocyanate to alkenes, 3567 Thio compounds 1. 2-dithiol-3-thiones. anodic oxidation, 771 1, 2-dithiolylium ions, cathodic reduction, 767 1, 2-dithiolylium salts, diaryl, photochem., 5213 methanethiol and ethanedithiol with a-chloroisatin, 307 N, N’-diisopropyl thioacetamide, 3843 N, N’-thiobisphthalimide, sulphur transfer reagent, 1481 S-methyl thioimidates, confiiration, 2655 thioacylation, 2777 thioamides, 3977 vinylogues with organomagnesiums, 347 1 thioaroyl-thiocyanate and isothiocyanate, 15 13 thiocarbonyl ylides and imines, trithiones, 1159 thiocyclohexyl free radicals, transannular participation, 339 thioketals, cleavage, 1085 thiolactams, 4 19 1 thiolactones, 543 thiolo+actones, CD, 3 165 thiosulphinates, NMR shift reagents, 3907 tritylthionitrite, deoxygenation, 3405 Thiophenes acetylene cycloaddition, 5269 benzo[e] -2-methyl[ 11benzothieno [3,4-bcl thiinne, 81 benio( l)th
xxx

Ultra-violet apectn Thbphenes (continued) 2-(5-phenyl-1, 2dithiole3-ylio) 6,7-benzo-4.9-oxido[ l l ] annulenes, 4 129 phenolate, 4687 reduced dibenzothiophen, photoC,C, cyclanones with BF, ,4553 ethylacetoacetate, keto-enol chemical rearrangement, 255 tautomerism, 40 17 ring enlargement, 3647 linear non-planar polyenes, 597 to a thiepin, 3647 quinolines, 1555 thiene-1, l-dioxide, photolysis, 4781 ureas thieno[ 3,2-b] - , 3847 1, 3-dimethyl - , 15Nlabelled, carion and anion radicals, 3847 NMR of BF, and SbCI, adducts, tram- and c&-l, a-dithiolane-l227 oxide, 203 N-nitroso-N-methyl - , base invalence bond isomerism, 1429 duced decomposition, 5 147 l”m compounds Schmidt reaction on camphor, tributyltin hydride, cyclization of 187 unsaturated acyl chlorides, 749 synthesis, o-adds of isonitriles, Toxins 4263 surugatoxin, 2545 thiourea dioxide, reducing agent, participation, S atom in thiacyclo343 hexyl free radicals, 339 vinylogous, dehydration, 15 19 lkansition states 1-arylethylammonium ions with sodium ethoxide, 9 17 polarity, enol ether iodination, 3629 Vinyl groups Triazines allenyl magnesium, 4465 triazolo( 5. I-c] -a*triazines, 47 19 amines, enamine equilibria, 2837 Triazolea indolizines, 2607 amino - , N-amidino hydrazonyl @-methyl-p-nitrostyrene with bromide addition, 3943 benzene, 2829 I-chlorobenzo - , oxidation of thioamide vinylogues with organosulphides, 50 1 magnesiums, 347 1 Triazolines vinylencarbonates, chelotropic norbornyl endo Al-l, 2, 3-triareactions and M.O. calculations, zoline, 28 19 1119 Tropolones Vitamins crowded, 3, 5, ‘I-tribromohinokila, 25-dihydroxycholecalciferol, to1,741,745 4147 Troponoid compounds and ylids, biphenyl synthesis, 4985 benzo[ 3,4] cyclobuta[ 1,2] tropolone S, lium cation, 4859 X-ray analysis cycloaddition with maleic anhy8-acetoxy-6-(2,4-dimethoxy-5dride, 2685 bromophenyl)-3-methyltriI-methoxyhomotropylium cations, cyclo[5.2.1.03”‘] decan-l-one, 5 4399 5059 2-methoxy - , with I-oxoheptaanomalous scattering, 1323 fulvene, 4379 axivalin, sesquiterpene lactone, 8-oxoheptafulvalene and - , 869 4423 tropone, methyl- and phenylful1, 8-bishomocubane rearrange vene cycloadditions, 2297 ments, 49 13 tropylium ions with chromous corynoline p-bromobenzoate, alions, 4989 kaloid, 3729 Twi&mes daphnilactone A, alkaloid, 1275 CD, failure of octant rule, 4275 4-tosyloxy - , solvolysis, 699 2(i, 6-dimethyl-phenyl)-iminotricyclo[4.4.0.03’*J decane, op3(2-chlorobenzoyl)-thiazolitical rotation, 4355 dine, 3179

Tetrahedron

Letters 1972

X-ray analysis (contimed) layered cyclophane, 498 1 methyl naphthalene-2-carboxylate photodimcr, 472 1 nickel-ligand catalysts, 1457 2-(5-phenyl-I, 2-dithiole-3-ylio) phenolate, 4687 retigeranic acid, scsterterpene, 4609 rhazinilam, alkaloid, 909, 9 13 surygatoxin, indolc alkaloid, 2545 swazine, alkaloid, 5 183 spiro dilactone alkaloid, 707 7-syrl-6-endo-dihydroxybicyclo [ 2.2.11 heptane 2-endo-carboxylic acid-a-kictone, 35 1 tropolones, crowded, 741 2-troponylethoxycarbonylmethylenetriphenylphosphonium betaine, 16 11

Ylides aziridinium - , fragmentation, 3827.4659 cyano 2-azapropenide, 477 1 cyclization giving dihydroindolizines, 2585 dibenzocyclononatetraene phosphonium ylide, 3361 dimethyloxosulphonium - ,4453 enolate - , condensation with ketones, 933 general prep., 2635 isoquinolinium - , 3325 new stable carbonium ions, 4851 N-vinyliminopyridinium - , with alkynes, 5245 phenylthiomethyl-ammonium, and sulphonium, 3587 sulphonium - , of dithianes, 989 thiocarbonyl - , 1159 Ynamines addition to nitro compds., 41 cycloaddition to CO,, carbamoyl and keto-alkoxy-ietenes and alcoyl isocyanates, 1131, 1135, 1139 methylenecyclopropenes, and, 3969