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39015007149886
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TOPICS IN
ORGANIC
CHEMISTRY

Sheldon Emery Professor

of Organic Chemistry
Harvard University

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Mary Fieser
Research Fellow in Chemistry
Harvard University

New York

REINHOLD PUBLISHING
Chapman

CORPORATION

& Hall, Ltd., London

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Copyright

1963

PRINTED IN THE UNITED STATES

by

REINHOLD PUBLISHING CORPORATION

All rights reserved

Library of Congress Catalog Card Number:

63-13444

OF AMERICA

PREFACE

Having included in the manuscript for Advanced Organic Chemistry (1961) most
in beginning and advanced courses of a general

of the topics usually considered

it was still of reasonable

which appeared in Organic
At the time we had no plans for revision of these
Chemistry, 3rd edition (1956).
chapters or for any imminent extension of the Advanced book, but eventually a
plan emerged for combining a revision of the 1956 chapters with a supplementation
to the 1961 book.
The present book is the outcome.
Part I includes nine chapters on subjects which are necessarily specialized but
which form important parts of the general field.
Most of the topics concerned are
active
In
under
some
cases
the situation has changed so
currently
investigation.
much in recent years that chapters had to be rewritten in toto or in large part.
The chapter on Steroids was rewritten in narrative style. The chemistry of
rubber is transferred to Terpenoids and the chapter on Synthetic Polymers is
limited to man-made elastomers, plastics, and resins, arranged according to
Much of the chemistry of dyes is historical and
polymerization mechanisms.
nature,

we decided to bring the book to a close while

and

length

remains

to omit several

unchanged,

special-topic

but modern

chapters

covalently-bonded dyes were introduced

less

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than a decade ago.

The sections of Part I are numbered in extension of those of Advanced for con
venience in cross referencing.
Thus 31.48 designates the last section of Advanced
and 32.1 refers to the first section of the present book.

page of the first book, e.g. 963, is entered as Adv., p. 963.

reference to a specific

cross reference to a

page within the present book carries no appendage.

Part

II

includes

a few corrections

to Advanced and a few topics which should

have been included originally (adamantane,

and S specification

of configuration,

However, most of the entries describe advances reported in the literature

We have scanned
1, 1961, the closing date for coverage in Advanced.
for
fit
the
the principal journals
into
framework of Advanced and
papers which
which seem to us significant and interesting, and have included in Part
accounts
of the new work as supplements to the material previously published.
As a check
on the accuracy of our accounts, copies for review were sent to the principal in
vestigator of each research group involved. It is a pleasure to report that the
response was unanimous and that the corrections and suggestions were very
helpful. We thank the many chemists who contributed in this way to the produc
tion of an accurate survey of recent research.
We are very much indebted also to the following specialists for reviewing
chapters or sections of Part I and presenting invaluable advice :
etc.).
since

July

II

iii

iv

PREFACE

V. Boekelheide
J. A. Boothe
H. Brockmann
C. J. W. Brooks
E. Clar
A. C. Cope
O. C. Dermer
L. Farkas

R. M. Herbst
W. Herz
C. H. Hochwalt
R. Huisgen

L. Marion
M. S. Newman

M. D. Softer
E. C. Taylor
W. I. Taylor

W. D. Ollis
I. Ugi
S. W. Pelletier
I. M. Hunsberger F. W. Quackenbush
E. E. van Tamelen
P. Karrer
H. J. Ringold
B. C. L. Weedon
R. Kuhn
E. F. Rogers
E. Wenkert
R. V. Lawrence
T. F. Sanderson
K. Wiesner
Leavitt
H.
E.
G. Fodor
Schroeder
W.
C. Wildman
J. J.
R. Grewe
E. Leete
A. M. Seligman
We thank Makhluf J. Haddadin and Musa Z. Nazer for careful reading of the

page proof.

The expense of preparing the many Xerox copies of manuscript that went out
for prepublication review was defrayed by a grant from Research Corporation.
New biographies are included in both Parts I and II. An asterisk is appended
to the first entry in the book of the name of a chemist whose biography appears in
Advanced Organic Chemistry.
The author index provides a guide to biographies
published
previous

in both books.
space-saving

References

in the text throughout the book follow the

style of citing the date and the name of the senior author,

if known to us, or of the first author listed.

Part

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of recent date and includes authors' names as

II is documented

with references
they appear in the literature; the

short-form journal abbreviations used are listed in the glossary.

The coverage of the book extends through the major journals which reached us
Future plans depend upon the reception of Part II
by the date given below.
of the present book.
We welcome advice, as well as corrections and suggestions.
Lou1s F. F1eser
Cambridge, Massachusetts
Mary F1eser
January 1, 1963

GLOSSARY

SOLVENTS

Al

Methanol or ethanol

Di

An
Chf

Acetone

DMF Dimethylformamide

H2O

Chloroform

EtOH Ethanol

CgH6

Benzene

Hex

MeOH Methanol
Pyridine
Py

Hexane

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REAGENTS,

NBA N-Bromoacetamide
NBS N-Bromosuccinimide

DNF

AcOH Acetic Acid

Dioxane

Water

REACTIONS

TNM Tetranitromethane

2,4-Dinitrofluorobenzene

OH+ ArCO3H

TsCl />-Toluenesulfonyl chloride

TsOH ^-Toluenesulfonic acid
W.-K. Wolff-Kishner reduction

GROUPS

Ac

Acetyl

Cb Carbobenzoxy

/-Bu
Et Ethyl
/-Butyl
Me Methyl
Bz
Benzoyl
Cathyl Carbethoxyl Ms Mesyl,
Ph

CH3SO2

Phenyl

Phth Phthaloyl

Ph,C Trityl,
Pr
Propyl
Ts
Tosyl,

(C^3C^-CH3C6HsSO2-

vi

GLOSSARY

CONSTANTS

Specific rotation for sodium

aD

reported as

line at or near 250, conventionally

[a]i>.

Molecular rotation (units, not degrees) = aD X mol. wt./lOO.

(a) Ultraviolet (UV) absorption maximum in rmi determined in
ethanol or valid for an ethanolic solution. The molecular extinc
tion coefficient, e, or log , is given in parentheses, (b) Infrared
(IR) absorption maximum in n.

MD
X

cm-1

or wave number, of an

Frequency,

IR

absorption

band.

cps

Cycles per sec. (nuclear magnetic resonance spectra).

kcal./mole

Kilogram calories per mole.

BONDS

Full

line

Dotted line

up, or to the front

Wavy

down, or to the rear

No

bond

configuration unknown
epimer mixture
,

SYSTEMATIC NAMES

chemical name is divided only when each part is a correctly pronounceable

word

in its own right. Examples:

1.

A2-Octene (or 2-octene or octene-2). Not oct-5-ene (oct is not a word).

(or 5-cholestene-3/3-ol). Not cholest-5-en-3^-ol (en is
not a word, as is ene, and is pronounced differently; ol is a word. Other

2. A6-Cholestene-3/3-ol

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3.

endings used as words: diene, triene, diol, polyol).

Cholestanyl acetate. Not cholestan-3/3-yl acetate (cholestan is not a word,
yl is not a word).
Also correct: cholestane-3/3-ol acetate (to be read in the sense "cholestane3/3-ol, acetate of". The same form is appropriate for estrone acetate,
cholic acid triacetate, cortisol 21-acetate.
DEVIATIONS

2-Desoxo3-Desoxy-

Lacking
Lacking

Homo- (acid)
Nor- (acid)
Bisnor- (acid)

FROM USUAL STRUCTURE

a 2-keto group
a

3-hydroxyl group

CH2CO2H
CO2H extended to
CH2CO2H
CH2CH2CO2H shortened to
shortened
to
CH2CH2CO2H
CO2H
SPECIFIC TO STEROIDS

7-DehydroD-Homo-

A-Nor18-Nor19-Nor2,3-Seco-

2,3-Seco-2,3-dioic

,8-Olefinic derivative

Ring D expanded to a six-membered ring

Ring A contracted to a five-membered ring
Lacking the methyl group at Cn
Lacking the methyl group at C1o
2 ,3-Bond severed and hydrogen added at C2 and C3
2,3-Bond severed, C2 and C3 converted to CO2H groups

vii

GLOSSARY

NOTE ON SPELLING
Since chemical names should be and usually are pronounced

as they are spelled,

we prefer use of dioxane, furane, tryptophane, and urethane, since the pronuncia
tion is stronger

For the same reason we favor

than with the -an equivalents.

desoxo- and desoxy- over deoxo- and deoxy-.

EUROPEAN

TERMS

ETH

Eidgenossische

MPI

Institute of Technology)
Max-Planck-Institut
fur Biochemie

KWI

Kaiser- Wilhelm-Insti tut

Geheimrat

Title

Habilitationsschrift

Independent postdoctoral research publication required

for appointment as Privatdozent
Post equivalent to that of an assistant or associate pro

Technische

Zurich

Hochschule,

(Swiss

Federal

(Medizinische

For-

II;

now

schung)
(before

World

War

MPI)

Privatdozent

of special academic distinction in Germany

fessor

AG.
BASF
Ciba

(Company)
Badische Anilin-und Soda-Fabrik (Germany)
Gesellschaft fur Chemische Industrie, Basel, Switzerland

SASM

Societe d'Applications scientifique

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UCLAF

Aktiengesellschaft

Usines chimiques

et mecanique

des Laboratoires Francais

JOURNALS

Journal of the American Chemical Society

Angewandte Chemie
Annalen der Chemie
Annales de chimie (Paris)
Chemische Berichte (formerly Berichte der deutschen chemischen Gesellschaft)
Bulletin de la societe chimique de France

Acta Chemica Scandinavica

Collection of Czechoslovak Chemical Communications
Comptes rendus hebdomadaires

des seances de l'academie des sciences

Gazzetta chimica italiana

Helvetica Chimica Acta
Journal of the Chemical Society (London)
Journal of Organic Chemistry
Monatshefte fiir Chemie
Recueil des travaux chimique des Pays-Bas (The Netherlands)

viii

GLOSSARY

BIOCHEMISTRY
Adenosine

9-/3-D-Ribofuranosyladenine,

AMP
ADP
ATP

Adenosine-5'-monophosphate,
Adenosine-5'-diphosphate,

a nucleoside

adenylic
a

acid, a mononucleotide

dinucleotide

Adenosine-5'-triphosphate, the principal biological phosphorylating agent and repository for chemical energy
Diphosphopyridine nucleotide (formerly called coenzyme I), a
dinucleotide composed of AMP joined through a diphosphate

DPN

linkage

DPNH
TPN

Reduced

to l-/3-D-ribofuranosylnicotinamide-5'-phosphate

DPN

Triphosphopyridine nucleotide (formerly called coenzyme II),

DPN with an additional phosphate ester group at the 2'-position in the adenosine unit
Flavin adenine dinucleotide, a dinucleotide composed of AMP

FAD

joined

through

a diphosphate

linkage

to riboflavin-5'-phos-

phate

FADH

Reduced

RNA

Ribonucleic acid,

polymer of ribose nucleotide monophosphates

joined together by phosphate linkages between 3'- and 5'-hydroxyl groups
Desoxyribonucleic acid, a polymer of 2-desoxyribose nucleotide
joined together by phosphate linkages be
monophosphates
tween 3'- and 5'-hydroxyl groups
Coenzyme A, adenylic acid joined through a pyrophosphate
linkage to pantothenic acid, which is joined by a peptide link

DNA

CoASH
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FAD
a

to /3-mercaptoethanol

UDPG

Uridinediphosphoglucose

Pyrimidines:

Purines:

Cytosine

Adenine

Thymine :
Uracil

Guanine

CONTENTS
PART

Chapter
Polynuclear Hydrocarbons
Structure,
Phenanthrene,
Synthetic Routes,
Oxidation, 10.

Anhydride Synthesis, 3. Other

6.
Substitutions, 7.

Succinic

3.

Addition

5.

Reactions,

Structure and Reactivity, 10. Anthraquinones, Prepara

14.
Substitution Reactions, 16. Displacement
Reactions, 18. Polyunsaturated Derivatives, 20. Reduction Prod

Anthracene,

tion and Synthesis,

ucts, 20.

Insect Dyes and Bacterial Pigments, 24. Cochineal-Carminic

Kermes-Kermesic Acid, 24. Lac Dye-Laccaic Acid, 26.
24.
domycins,
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Polynuclear
Pentacene,
thracene,
38.

Acid,
Rho-

26.

Hydrocarbons,
Hexacene,
33.

Naphthaccne,

27.

Heptacene,

Picene,

Pyrene,

33.

Circumanthracene,

33.

31.

Perylene,

Hexabenzocoronene,

40.

27.

Chrysene,

30.

41.

Rubrene, 29.
1,2-Benzan-

36.

Coronene,

Natural Pig

ments, 42.
Carcinogenic

Structure,

Hydrocarbons,
Correlation

Discovery, 43. Carcinogenicity and

with Chemical Reactivity, 50. Syn

47.

thesis, 53.

Molecular Overcrowding,

56.

Chapter 2
Aromatic Heterocyclic Compounds
Five- and Six Membered Types,
60.

Resonance,

Reaction,

63.

Ring Fission,
Indole, 72.

66.

Types, 71.
Triazoles and Tetrazoles,
Salts, 77.

59.

Electrophilic

73.

Benzofuranes,

68.

Furane, Pyrrole, and Thiophene,

Substitutions, 65. Diels-Alder
Pyrrole Pigments, 69. Other

Phenylpentazole,
77.

Griseofulvin,
ix

76.
79.

Triaryltetrazolium
Butenolides,

81.

CONTENTS

Pyridine, Nucleophilic Substitutions and Displacements, 82. Electrophilic Substitution, Oxidation, 84. Quaternary Salts and Hydrox
Ring Fission of Pyridinium Salls,
ides, 85.
Pyridine-N-Oxide, 86.
89.
Production of Pyridine Derivatives, 90. Synthesis of Pyri
dines, 91.
Quinoline and Isoquinoline, Preparation, 91. Properties,
96.

Other
103.

Dehydroquinolizinium Salts, 97.

98.
Pteridines,
Heterocycles,
Coumarins, 104. Chromane,

99.

Sydnones,

101.

Pyrones,

Xanthone,

Chromone,

105.

Anthocyanins, 106. Flavones and Isoflavones, 108.

116.
Boron Het
Pigments, 115. Ommochromes,

Khellin, 105.
Miscellaneous
erocycles, 117.

Chapter 3
Alkaloids
Isolation,
Alkaloids, 121.

Degradation, 120. Pyrrolidines, 12.

Senecio
Piperidine Derivatives, 123. The Pelletierines, 124.
Tropane Alkaloids, 127. Benzylisoquinolines, 131.
Morphine, 133. Cinchona Alkaloids, 142. Hydroisoquinolines, 142.
Lupine Alkaloids, 143. PhenanthroquinoIpecac Alkaloids, 143.
lizidines and Phenanthroindolizidines, 145. Amaryllidaceae Alka

Occurrence

and

119.

loids, 146.
153.
Alkaloids, 147. Yohimbe Alkaloids, 151. Oxindoles,
Strychnine, 154. Curare Alkaloids, 155. Ergot Alkaloids, 157.
Erythrina Alkaloids, 158. Aconite-Garrya Alkaloids, 159. Calycanthine and Chimonanthine, 161.
Alkaloid Biosynthesis, 162.

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Indole

Chapter 4
Terpenoids
Isoprene

Rule,

and Aldehydes,

Hydrocarbons
Monocyclic Ketones,

Terpene

168.
171.

Bicyclic Terpenes,

(C10),

169.

172.

Rearrangement

C1o-Alcohols
of

Camphor, 176. Cantharidin, 179.

Bicyclic ds-Terpenes, 184.
Sesquiterpenes (Cm), Acyclic, 184.
Diterpenes (C20), 191. Phytol, 191. Resin Acids, 192. Sclareol Group,
197.
Gibberellic
Fichtelite. 199. Cafestol, 200.
Cembrene, 200.
Acid, 200.
175.

Triterpenes (C30), 202.

Polycyclic Triterpenoids, 202.
Squalene, 202.
Carotenoids (C40), 205.
205.
Carotenes,
Lycopene, 208. cis-transBixin, 210.
Isomerism, 209.
Crocetin, 211. Xanthophyll Alcohols
and Epoxides,

211.

Ketonic Carotenoids,

noids, 215.

Biosynthesis of Terpenes,

222.

Rubber,

222.

212.

Synthesis

of Carote

CONTENTS

Chapter 5
Steroids

225

and Bile Acids, 225.

Vitamin D, 231. Estrogens, 234. An

240.
244.
Adrenocortical Hormones, 245.
drogens,
Progesterone,
251.
19-Norsteroids,
Hormone Production, 253. Hormone Ana
Cardiac Glycosides, 265. Alkaloids, 271.
logs, 262.

Sterols

Chapter 6
Vitamins

277

Thiamine (Vitamin B1), 280.

Riboflavin (Vitamin
Vitamin Bs (Pyridoxine), 284. Nicotinic Acid, 286.
Vitamin B12, 288. Pantothenic Acid,
Pteroylglutamic Acid, 287.
290.
Biotin, 291.
Vitamin A, 293.
Physiological Functions of
Vitamin A, 296. Tocopherols, 298. Vitamin K, 300.

Discovery,
B2),

277.

282.

Chapter 7
Chemotherapy
Organic Arsenicals,
Antimalarials, 307.

304

Germanin,

304.

Sulfonamides,

305.

309.

Neomycins B and C, 318.

Macrolides, 320. AntimycinA, 324. Cycloheximide
phenicol, 319.
and Nonactin, 325.
Actinomycin,
Polypeptide Antibiotics, 325.
327.
Other
Sideraminesand Sideromycins, 327.
Mitomycin A, 328.
cin, 317.

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Amebicidal Drugs,
Penicillin, 313. Streptomy
Chloram
Tetracyclines, 318.

306.

Antibiotics,

329.

Cancer Chemotherapy, 330.

Chapter 8
Synthetic Polymers
Polymer Types,

334

Polyamides,
Condensation Polymerization,
Addition
Polyurethane Elastomers, 338.
Radical Polymerization,
Polymerization of Vinyl Monomers, 339.
339.
Ionic Catalysis, 340.
Polyethylene, 342. PolytetrafluoroPolyvinyl Halides, 344.
Poly
ethylene, 342.
Polystyrene, 343.
344. Polyacrylates, 345.
344.
vinyl Acetate,
Polyacrylonitrile,
Copolymerization, 347.
Stereospecific Polymerization of Olefins, 345.
Polymerization of Dienes, 348. Polyoxymethylene, 351.
Ion-Ex
Synthetic Resins, 351.
Phenol-Formaldehyde Resins, 352.
MelamineUrea-Formaldehyde Resins, 353.
change Resins, 353.
336.

334.

Polyesters,

335.

337.

Formaldehyde Resins,
355.

354.

Epoxy Resins, 356.

Alkyd Resins,

354.

Polyester Resins,

xii

CONTENTS

Chapter 9
Dyes
Direct Dyes, 358.
Color and Constitution, 357.
Vat Dyeing, 360.
Formation of Dye
Mordant Dyeing, 360.
Substantive Dyes, 361.
on the Fiber, 362.
Printing, 362.
Perkin's Mauve, 363.
Rosaniline Dyes, 364. Aurin, 367.
The Phthaleins, 368.
Synthetic Alizarin, 371.
Polyhydroxyanthraquinones, 373.
Anthraquinone Dyes for Wool and for Hydrophobic Fibers, 374.
Other Indigoid Dyes,
Synthetic Indigo, 375.
Tyrian Purple, 378.

357

378.

Indanthrone,

Algol Colors,
thrones,

Dyes,

389.

389.

Flavanthrone,

381.

Benzanthrone

382.

Carbazole
Types,
Dithiazolanthraquinone

387.

387.

390.

Dibenzpyrenequinones,

Dyes,

Dialkyl
389.

Dyes,

384.

DipyrazolanAnthranthrone

Tetracarboxyimide Dyes,

Sulfur Dyes, 391.

Acidic and Basic Azo Dyes, 393.
Dyes, 400. Chrome Dyes, 402.
390.

Azoic
Substantive Azo Dyes, 396.
Disperse Azo Dyes, 404.
Diazacyanines, 407. Color Photography, 410.

Cyanine Dyes, 405.

Reactive Dyes, 411.
Phthalocyanines,

Brighteners,

413.

Lacquer

Pigments,

415.

415.

PART

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(New sections alone are listed here.)

R and S Specification of Configurations, 422. Hydrogenolysis, 431. Reduction

with Diimide, 432.
Imidazolide Synthesis
Trishomocyclopropenyl Cation, 448.
of Carbon yl Compounds, 456.
Nitration of Ketones, 459.
Peroxidation of
Ketones, 462. Reduction of Ketones, 463.
Cleavage of Phenylhydrazones and
Enol Ethers, 467.
Reduction of a ,/3-Oxido Ketones, 478.
Semicarbazones, 464.
Ethylation of Amines,
Phosphonate Modification of the Wittig Reaction, 482.
Diazirine,
486.
Acetylenic Amines, 487. Liquid Ion-Exchange Systems, 489.
Adamantane, 506.
Twistane, 510.
Optically Active Cycloalkenes and
Aromatic Hydrocarbons from 2-Pyrones, 519. Light-Catalyzed
Dienes, 512.
of Esters, 536.
of Allylic
Lichen Dyes, 538.
Rearrangement
Rearrangement
Acids,
Oxidative Decarboxylation of
Alkali Cleavage of
Sulfones, 541.
545.
2 ,6-Dihalobenzaldehydes,
553.
554.
Diaza2 ,3-Diphenylindenone
Oxide,
493.

quinones,

556.

Octaphenylcubane,

572.

Pseudoaromatic

Heterocycles,

578.

Thiophene
Synthesis of Arachidonic Acid, 584.
Natural OleVinyl Ketone Synthesis of Acids, 589.
finic Hydroxy Acids, 590.
Distribution of Fatty Acids in Natural Glycerides, 591.
Scent Attractants and Repellents of Insects, 596.
Lipids of the Honeybee, 593.
Kallidin and Bradykinin, 612.
Peptide Synthesis from Acid Hvdrazides, 610.
Synthesis

of n-Rhamnose,

Synthesis

of Acids, 587.

Depsipeptides,

613.

581.

Selective Chemical

Cleavage of Proteins, 617.