Journal of Organometallic Chemistry 624 (2001) 404– 406 www.elsevier.nl/locate/jorganchem
Contents of Volume 624 Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Mini-Accounts Carbon nucleophile addition to sp2-unsaturated Fischer carbene complexes J. Barluenga, J. Flo´rez, F.J. Fan˜ana´s . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Contra-intuitive stereocontrol: endo-selective nucleophilic additions on an arene– tricarbonylchromium template A. Sarkar, S. Ganesh, S. Sur, S.K. Mandal, V.M. Swamy, B.C. Maity, T.S. Kumar . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Addition– b-elimination: a new method for the preparation of organometallic compounds A. Liard, J. Kaftanov, H. Chechik, S. Farhat, N. Morlender-Vais, C. Averbuj, I. Marek . . . . . . . . . . . . . . . . . . . . . . . . .
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Studies on regioselective addition of benzylic organometallics to a-oxoketene dithioacetals in our aromatic annelation protocol H. Ila, H. Junjappa, O. Barun. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
34
On the evolution of organozinc carbenoid chemistry from carbonyl compounds — a personal account W.B. Motherwell . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Regular Papers Oxidation of organometallic compounds (RM, M =Li, MgBr, ZnBr, CuCNLi, Cu(R)CNLi2) with tBuOOLi, Ti(OiPr)4- mediated with t BuOOH, and with O2, to give alcohols (ROH). Are radicals R involved? M. Mo¨ller, M. Husemann, G. Boche . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Generation of allylic and benzylic organolithium compounds by fluorine– lithium exchange: reaction with electrophiles D. Guijarro, M. Yus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
54
A single-strand polymer of hexacoordinated zinc(II) phosphodiester complex A. Angeloff, J.-C. Daran, J. Bernadou, B. Meunier . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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W(CO)6-Mediated desulfuroligomerization of bis-dithioacetals. New synthesis of substituted oligo(phenylene– vinylenes) C.-W. Shiau, C.K.F. Shen, W. Pan, C.-H. Kuo, S.C. Kao, T.-Y. Luh . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
64
Silyl-cupration of a propargylsilane as a test for the reversibility of a metallo-metallation M. Angeles Cubillo de Dios, I. Fleming, W. Friedhoff, P.D.W. Woode . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
70
The rhodium-catalyzed Pauson–Khand reaction T. Kobayashi, Y. Koga, K. Narasaka . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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New preparation of benzylic zinc reagents via a fragmentation reaction C. Piazza, N. Millot, P. Knochel . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
89
Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via ( −)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation H. Laqua, R. Fro¨hlich, B. Wibbeling, D. Hoppe . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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A new approach to b-functional phospholes. Application to the synthesis of a b-CH2CH2-bridged diphosphole disulphide B. Deschamps, F.-X. Buzin, A. Avarvari, F. Nief, F. Mathey . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
106
Synthesis and structure analysis of tricarbonyl[tetrakis(1%-methylcyclopropyl)cyclobutadiene]iron(0) I. Emme, T. Labahn, A. de Meijere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Contents of Volume 624 Journal of Organometallic Chemistry 624 (2001) 404–406
405
Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature M. Alami, B. Crousse, F. Ferri . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Bimetallic p-conjugated complexes modulated by a carbonyl spacer: synthesis of arenetricarbonylchromium– ferrocene derivatives D. Prim, A. Auffrant, Z.F. Plyta, J.-P. Tranchier, F. Rose-Munch, E. Rose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
125
Iron catalyzed hydrodebromination of 2-aryl-1,1-dibromo-1-alkenes M.A. Fakhfakh, X. Franck, R. Hocquemiller, B. Figade`re . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex T. Shimada, N. Asao, Y. Yamamoto . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Regioselective alkylzirconation of internal alkynes S. Yamanoi, K. Seki, T. Matsumoto, K. Suzuki . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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A highly efficient and practical preparation of 2,4-pentadienyltitaniums and their g-selective addition reaction with aldehydes and ketones S. Okamoto, F. Sato . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
152
Synthesis of novel 1,1%-bis(oxazolinyl)metallocenes and their application in the asymmetric phenyl transfer from organozincs to aldehydes C. Bolm, N. Hermanns, M. Kesselgruber, J.P. Hildebrand . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
158
Chiral 1,2-bis(phosphetano)ethanes A. Marinetti, S. Jus, J.-P. Geneˆt, L. Ricard . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen M. Ma˛kosza, M. Surowiec . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Organotransition metal modified sugars: Part 22. Direct metalation of glycals: short and efficient routes to diversely protected stannylated glycals C. Ja¨kel, K.H. Do¨tz. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Transition-metal catalyzed synthesis of d-hydroxy-g-lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via g-unsaturated carboxylic acids. Comments on the formation of a-cyclopropyl carboxylic acids H. Rudler, P. Harris, A. Parlier, F. Cantagrel, B. Denise, M. Bellassoued, J. Vaissermann . . . . . . . . . . . . . . . . . . . . . . . .
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Controlled monohalogenation of phosphonates: Part IV. Selective synthesis of monohalogenomethylenediphosphonates B. Iorga, P. Savignac . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
204
Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid F. Homsi, K. Hosoi, K. Nozaki, T. Hiyama . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Rate and mechanism of the reversible formation of a cationic (h3-allyl)palladium(II) complex in the oxidative addition of allylic acetate to a palladium(0) complex ligated by diop: an unusual behavior C. Amatore, S. Gamez, A. Jutand . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Stereoselective addition of organomanganese reagents to chiral acylsilanes and aldehydes C. Boucley, G. Cahiez, S. Carini, V. Cere`, M. Comes-Franchini, P. Knochel, S. Pollicino, A. Ricci . . . . . . . . . . . . . . . . . . .
224
Carbon– carbon bond formation via oxidative-addition processes of titanium(II) reagents with p-bonded organic substrates. Reactivity modifications by Lewis acids and Lewis bases: Part 22. Organic chemistry of subvalent transition metal complexes J.J. Eisch, J.N. Gitua, P.O. Otieno, X. Shi . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Asymmetric allylboration for the synthesis of b-hydroxy-d-lactone unit of statin drug analogs M.V. Ram Reddy, H.C. Brown, P.V. Ramachandran . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Palladium catalyzed cyclization reactions of acetylenic lactams W.F.J. Karstens, M. Stol, F.P.J.T. Rutjes, H. Kooijman, A.L. Spek, H. Hiemstra . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Rhodium-catalysed asymmetric ring opening of oxabicyclic alkenes with heteroatom nucleophiles M. Lautens, K. Fagnou, M. Taylor, T. Rovis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Chiral platinum and palladium complexes containing functionalized C2-symmetric bisaminoaryl ‘Pincer’ ligands M. Albrecht, B.M. Kocks, A.L. Spek, G. van Koten . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Contents of Volume 624 Journal of Organometallic Chemistry 624 (2001) 404–406
Synthesis and characterization of organotin triflate clusters A. Orita, J. Xiang, K. Sakamoto, J. Otera. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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The BF3 and B(C6F5)3-catalyzed 1,3-isomerization of allylic stannanes J.A. Marshall, K. Gill . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Synthesis of substituted cyclopropanone acetals by carbometallation and its oxidative cleavage with manganese(IV) oxide and lead(IV) oxide M. Nakamura, T. Inoue, E. Nakamura . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
301
Reactivity of lithium diphenylphosphonium diylides towards phosphorus electrophiles: Synthesis of a,b-unsaturated phosphorus compounds M. Taillefer, H. Jean Cristau, A. Fruchier, V. Vicente . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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A short synthesis of ( −)-dendrobine. Some observations on the nickel mediated radical cyclisation and on the Pauson– Khand reaction J. Cassayre, S.Z. Zard . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols J. Cossy, S. BouzBouz, A.H. Hoveyda . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Direct use of chiral or achiral organophosphorus boranes as pro-ligands for transition metal catalyzed reactions C. Darcel, E.B. Kaloun, R. Merde`s, D. Moulin, N. Riegel, S. Thorimbert, J. Pierre Geneˆt, S. Juge´ . . . . . . . . . . . . . . . . . . .
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Neutral, non-racemising, catalytic aerobic oxidation of alcohols I.E. Marko´, A. Gautier, J.-L. Mutonkole, R. Dumeunier, A. Ates, C.J. Urch, S.M. Brown . . . . . . . . . . . . . . . . . . . . . . . .
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Communications Nickel-catalysed three-component connection reaction of a phenyl group, conjugated dienes, and aldehydes: stereoselective synthesis of (E)-5-phenyl-3-penten-1-ols and (E)-3-methyl-5-phenyl-3-penten-1-ols K. Shibata, M. Kimura, K. Kojima, S. Tanaka, Y. Tamaru . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Self-organization of a rigid a,v-bis-silanediol determined by X-ray crystal structure F. Carre´, G. Cerveau, R.J.P. Corriu, B. Dabiens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Synthesis of ( −)-coniine and ( −)-pipecoline using ruthenium catalyzed ring closing metathesis K. Pachamuthu, Y.D. Vankar . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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On the steric course of transmetallations on enantiomerically defined a-carbamoyloxy organolithiums K. Tomooka, H. Shimizu, T. Nakai . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Hydrosilylation of aldehydes and ketones catalyzed by [Ph3P(CuH)]6 B.H. Lipshutz, W. Chrisman, K. Noson . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Cross-coupling of vinylpolysiloxanes with aryl iodides S.E. Denmark, Z. Wang . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Versatile palladium-catalyzed arylation of organomanganese chlorides by aryl bromides E. Riguet, M. Alami, G. Cahiez. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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1,4-Bis(arylsulfonyl)dihydropyridines in synthesis. Enantioselective synthesis of 2,3,6-trisubstituted piperidines S. Carballares, D. Craig . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Reactivity of g-benzyloxyallyltins with cyclohexylidene glyceraldehydes F. Fliegel, I. Beaudet, J.-P. Quintard . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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TRISPHAT salts. Efficient NMR chiral shift and resolving agents for substituted cyclometallated ruthenium bis(diimine) complexes D. Monchaud, J. Lacour, C. Coudret, S. Fraysse. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Scandium perfluoroalkanesulfonate-catalyzed Diels–Alder reactions in an organic solvent S. Kobayashi, T. Tsuchiya, I. Komoto, J.-i. Matsuo . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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Author index of Volume 624 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Subject index of Volume 624 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Contents of Volume 624 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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