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ORGANIC CHEMISTRY: A SERIES OF MONOGRAPHS
ORGANIC A
SERIES
CHEMISTRY OF
MONOGRAPHS
E D I T O R
H A R R Y H. W A S S E R M A N Department of Chemistry Yale University New Haven, Connecticut
1.
Wolfgang Kirmse. CARBENE C H E M ISTRY, 1 9 6 4 ; 2 n d E d i t i o n , 1 9 7 1
2.
Brandes
H . Smith.
BRIDGED
13.
ner.
Michael
Hanack.
CONFORMATION
14.
D o n a l d J. C r a m . FUNDAMENTALS OF
15.
1 9 6 5 ; Walter
(Editor).
S.
OXIDATION
CHEMISTRY,
16.
PART
R.
ORTHO
ORGANIC
CHARGE-TRANS
COMPLEXES, 1 9 6 9
James P . Snyder ( E d i t o r ) . N O N B E N 1969;
AROMATICS,
VOLUME
I,
V O L U M E II, 1 9 7 1
ORGANIC
PART B, 1 9 7 3 ; PART
C,
17.
1978
6.
Foster.
ZENOID
Trahanovsky IN
R. FER
K e n n e t h B . Wiberg ( E d i t o r ) . OXIDA TION IN ORGANIC CHEMISTRY,
A,
R. H . D e W o l f e , CARBOXYLIC ACID DERIVATIVES, 1 9 7 0
CARBANION CHEMISTRY, 1 9 6 5
5.
POLYMERIZA
2, 1 9 7 2
THEORY, 1 9 6 5
4.
RING-FORMING
TIONS, PART A , 1 9 6 9 ; PART Β , 1; B ,
ARO
MATIC C O M P O U N D S , 1 9 6 4
3.
Robert J. Cotter a n d M a r k u s Matz-
C. H . Rochester. ACIDITY FUNCTIONS, 1970
F . Hudson.
STRUCTURE AND
18.
MECHANISM IN ORGANO-PHOSPHORUS
Richard J. Sundberg. T H E C H E M I S TRY O F I N D O L E S , 1 9 7 0
CHEMISTRY, 1 9 6 5
7.
A . William Johnson. YLID CHEMIS
19.
TRY, 1 9 6 6
8.
Jan Hamer
(Editor).
1,4-CYCLOAD20.
AND RELATED
COM
POUNDS, 1 9 6 7
11.
21.
G . Chiurdoglu
(Editor).
CONFOR
MATIONAL A N A L Y S I S , 1 9 7 1
M . P . Cava a n d M . J. Mitchell. C Y CLOBUTADIENE
I v a r U g i ( E d i t o r ) . ISONITRILE C H E M ISTRY, 1 9 7 1
H e n r i U l r i c h . CYCLOADDITION R E A C TIONS O F H E T E R O C U M U L E N E S , 1 9 6 7
10.
OF T H E HETEROCYCLIC
N-OXIDES, 1 9 7 0
DITION R E A C T I O N S , 1 9 6 7
9.
A . R. Katritzky a n d J. M . Lagowski. CHEMISTRY
22.
G o t t f r i e d Schill. C A T E N A N E S , R O T A X ANES, AND K N O T S , 1 9 7 1
Reinhard W . Hoffmann.
DEHYDRO-
BENZENE AND CYCLOALKYNES, 1 9 6 7
23.
M . Liler. REACTION M E C H A N I S M S IN S U L P H U R I C A C I D AND O T H E R STRONG
12.
Stanley R. Sandler a n d Wolf
Karo.
ORGANIC FUNCTIONAL
PREP
GROUP
ARATIONS, V O L U M E I, 1 9 6 8 ; V O L U M E II,
1 9 7 1 ; V O L U M E III, 1 9 7 2
ACID SOLUTIONS, 1 9 7 1
24.
J.
B . Stothers.
CARBON-13 N M R
SPECTROSCOPY, 1 9 7 2
O R G A N I C
25.
Maurice LINE
Shamma.
ALKALOIDS:
PHARMACOLOGY,
26.
T H E ISOQUINO-
REACTIVE
(Editor). O R
1978
OF
HETEROCYCLES,
VOL
1973
Paul N . Rylander. ORGANIC SYNTHE
39.
SYNTHESES,
VOLUME
II,
I,
40.
1979
R o b e r t Τ . Blickenstaff, A n i l C . G h o s h , a n d G o r d o n C . Wolf. T O T A L
41.
33.
Howard Alper (Editor). TRANSITION
42.
PYROLYTIC
AND F L A S H
TECHNIQUES,
Paul de Mayo (Editor). REARRANGE MENTS
IN
STATES,
VOLUME
II,
43.
IN O R
GANIC S Y N T H E S I S , V O L U M E I ,
GROUND I,
AND E X C I T E D 1980;
VOLUME
1980; V O L U M E I I I , 1980
Elliot N . Marvell. T H E R M A L
ELEC-
TROCYCLIC R E A C T I O N S , 1980
1976;
V O L U M E I I , 1978
34.
PYROLYTIC CHEMISTRY:
1980
Sidney D . Ross, M a n u e l Finkelstein, a n d Eric J. R u d d . A N O D I C OXIDATION, 1975
ORGANOMETALLICS
Brown.
I N ORGANIC
VACUUM
S.
S Y N T H E T I C I N T E R M E D I A T E S , 1975
METAL
F . C.
APPLICATIONS O F F L O W
and Lawrence
Melvin, Jr. S U L F U R Y L I D E S : E M E R G ING
Roger
METHODS
S Y N T H E S I S O F STEROIDS, 1974
M . Trost
Harry H . Wasserman and Robert W. Murray (Editors). SINGLET OXYGEN,
VOLUME
1980
Barry
1978;
V O L U M E I I , 1982
Karo.
VOLUME
1977;
Philip S . Bailey. O Z O N A T I O N I N O R GANIC C H E M I S T R Y , V O L U M E I ,
W I T H N O B L E C A T A L Y S T S , 1973
Stanley R. Sandler a n d Wolf
III,
32.
Arthur Greenberg and Joel F . Liebman, STRAINED ORGANIC MOLECULES,
1974;
31.
Eric Block. REACTIONS O F ORGANOS U L F U R C O M P O U N D S , 1978
INTERMEDIATES,
38.
POLYMER
30.
37.
MATIONS
SES
29.
DIN R E S E A R C H , 1 9 7 7
H. C . V a n der Plas. R I N G TRANSFOR U M E S 1 AND 2,
28.
Pierre C r a b b e ( E d i t o r ) . PROSTAGLAN
1972
1973 27.
36.
C H E M I S T R Y AND
Samuel P. M c M a n u s GANIC
C H E M I S T R Y
44.
Joseph
J. Gajewski.
HYDROCARBON
T H E R M A L I S O M E R I Z A T I O N S , 1981
R. A . Jones a n d G . P . Bean. T H E C H E M I S T R Y O F P Y R R O L E S , 1976
In 35.
Alan Lehr
P. Marchand and Roland Ε. (Editors). PERICYCLIC REAC
preparation Walter S. Trahanovsky ( E d i t o r ) . O X
TIONS, V O L U M E I , 1977; V O L U M E I I ,
IDATION
1977
V O L U M E 5, P A R T D , 1 9 8 2
IN
ORGANIC
CHEMISTRY,
SERIES
CHEMISTRY OF
MONOGRAPHS
E D I T O R
H A R R Y H. W A S S E R M A N Department of Chemistry Yale University New Haven, Connecticut
1.
Wolfgang Kirmse. CARBENE C H E M ISTRY, 1 9 6 4 ; 2 n d E d i t i o n , 1 9 7 1
2.
Brandes
H . Smith.
BRIDGED
13.
ner.
Michael
Hanack.
CONFORMATION
14.
D o n a l d J. C r a m . FUNDAMENTALS OF
15.
1 9 6 5 ; Walter
(Editor).
S.
OXIDATION
CHEMISTRY,
16.
PART
R.
ORTHO
ORGANIC
CHARGE-TRANS
COMPLEXES, 1 9 6 9
James P . Snyder ( E d i t o r ) . N O N B E N 1969;
AROMATICS,
VOLUME
I,
V O L U M E II, 1 9 7 1
ORGANIC
PART B, 1 9 7 3 ; PART
C,
17.
1978
6.
Foster.
ZENOID
Trahanovsky IN
R. FER
K e n n e t h B . Wiberg ( E d i t o r ) . OXIDA TION IN ORGANIC CHEMISTRY,
A,
R. H . D e W o l f e , CARBOXYLIC ACID DERIVATIVES, 1 9 7 0
CARBANION CHEMISTRY, 1 9 6 5
5.
POLYMERIZA
2, 1 9 7 2
THEORY, 1 9 6 5
4.
RING-FORMING
TIONS, PART A , 1 9 6 9 ; PART Β , 1; B ,
ARO
MATIC C O M P O U N D S , 1 9 6 4
3.
Robert J. Cotter a n d M a r k u s Matz-
C. H . Rochester. ACIDITY FUNCTIONS, 1970
F . Hudson.
STRUCTURE AND
18.
MECHANISM IN ORGANO-PHOSPHORUS
Richard J. Sundberg. T H E C H E M I S TRY O F I N D O L E S , 1 9 7 0
CHEMISTRY, 1 9 6 5
7.
A . William Johnson. YLID CHEMIS
19.
TRY, 1 9 6 6
8.
Jan Hamer
(Editor).
1,4-CYCLOAD20.
AND RELATED
COM
POUNDS, 1 9 6 7
11.
21.
G . Chiurdoglu
(Editor).
CONFOR
MATIONAL A N A L Y S I S , 1 9 7 1
M . P . Cava a n d M . J. Mitchell. C Y CLOBUTADIENE
I v a r U g i ( E d i t o r ) . ISONITRILE C H E M ISTRY, 1 9 7 1
H e n r i U l r i c h . CYCLOADDITION R E A C TIONS O F H E T E R O C U M U L E N E S , 1 9 6 7
10.
OF T H E HETEROCYCLIC
N-OXIDES, 1 9 7 0
DITION R E A C T I O N S , 1 9 6 7
9.
A . R. Katritzky a n d J. M . Lagowski. CHEMISTRY
22.
G o t t f r i e d Schill. C A T E N A N E S , R O T A X ANES, AND K N O T S , 1 9 7 1
Reinhard W . Hoffmann.
DEHYDRO-
BENZENE AND CYCLOALKYNES, 1 9 6 7
23.
M . Liler. REACTION M E C H A N I S M S IN S U L P H U R I C A C I D AND O T H E R STRONG
12.
Stanley R. Sandler a n d Wolf
Karo.
ORGANIC FUNCTIONAL
PREP
GROUP
ARATIONS, V O L U M E I, 1 9 6 8 ; V O L U M E II,
1 9 7 1 ; V O L U M E III, 1 9 7 2
ACID SOLUTIONS, 1 9 7 1
24.
J.
B . Stothers.
CARBON-13 N M R
SPECTROSCOPY, 1 9 7 2
O R G A N I C
25.
Maurice LINE
Shamma.
ALKALOIDS:
PHARMACOLOGY,
26.
T H E ISOQUINO-
REACTIVE
(Editor). O R
1978
OF
HETEROCYCLES,
VOL
1973
Paul N . Rylander. ORGANIC SYNTHE
39.
SYNTHESES,
VOLUME
II,
I,
40.
1979
R o b e r t Τ . Blickenstaff, A n i l C . G h o s h , a n d G o r d o n C . Wolf. T O T A L
41.
33.
Howard Alper (Editor). TRANSITION
42.
PYROLYTIC
AND F L A S H
TECHNIQUES,
Paul de Mayo (Editor). REARRANGE MENTS
IN
STATES,
VOLUME
II,
43.
IN O R
GANIC S Y N T H E S I S , V O L U M E I ,
GROUND I,
AND E X C I T E D 1980;
VOLUME
1980; V O L U M E I I I , 1980
Elliot N . Marvell. T H E R M A L
ELEC-
TROCYCLIC R E A C T I O N S , 1980
1976;
V O L U M E I I , 1978
34.
PYROLYTIC CHEMISTRY:
1980
Sidney D . Ross, M a n u e l Finkelstein, a n d Eric J. R u d d . A N O D I C OXIDATION, 1975
ORGANOMETALLICS
Brown.
I N ORGANIC
VACUUM
S.
S Y N T H E T I C I N T E R M E D I A T E S , 1975
METAL
F . C.
APPLICATIONS O F F L O W
and Lawrence
Melvin, Jr. S U L F U R Y L I D E S : E M E R G ING
Roger
METHODS
S Y N T H E S I S O F STEROIDS, 1974
M . Trost
Harry H . Wasserman and Robert W. Murray (Editors). SINGLET OXYGEN,
VOLUME
1980
Barry
1978;
V O L U M E I I , 1982
Karo.
VOLUME
1977;
Philip S . Bailey. O Z O N A T I O N I N O R GANIC C H E M I S T R Y , V O L U M E I ,
W I T H N O B L E C A T A L Y S T S , 1973
Stanley R. Sandler a n d Wolf
III,
32.
Arthur Greenberg and Joel F . Liebman, STRAINED ORGANIC MOLECULES,
1974;
31.
Eric Block. REACTIONS O F ORGANOS U L F U R C O M P O U N D S , 1978
INTERMEDIATES,
38.
POLYMER
30.
37.
MATIONS
SES
29.
DIN R E S E A R C H , 1 9 7 7
H. C . V a n der Plas. R I N G TRANSFOR U M E S 1 AND 2,
28.
Pierre C r a b b e ( E d i t o r ) . PROSTAGLAN
1972
1973 27.
36.
C H E M I S T R Y AND
Samuel P. M c M a n u s GANIC
C H E M I S T R Y
44.
Joseph
J. Gajewski.
HYDROCARBON
T H E R M A L I S O M E R I Z A T I O N S , 1981
R. A . Jones a n d G . P . Bean. T H E C H E M I S T R Y O F P Y R R O L E S , 1976
In 35.
Alan Lehr
P. Marchand and Roland Ε. (Editors). PERICYCLIC REAC
preparation Walter S. Trahanovsky ( E d i t o r ) . O X
TIONS, V O L U M E I , 1977; V O L U M E I I ,
IDATION
1977
V O L U M E 5, P A R T D , 1 9 8 2
IN
ORGANIC
CHEMISTRY,