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TOPICS INORGANIC

CHEMISTRY

Sheldon Emery Professorof Organic ChemistryHarvard University

Mary FieserResearch Fellow in Chemistry

Harvard University

New YorkREINHOLD PUBLISHING CORPORATION

Chapman & Hall, Ltd., London

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Copyright © 1963 by

REINHOLD PUBLISHING CORPORATION

All rights reserved

Library of Congress Catalog Card Number: 63-13444

PRINTED IN THE UNITED STATES OF AMERICA

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7

PREFACE

Having included in the manuscript for Advanced Organic Chemistry (1961) mostof the topics usually considered in beginning and advanced courses of a generalnature, we decided to bring the book to a close while it was still of reasonablelength and to omit several special-topic chapters which appeared in OrganicChemistry, 3rd edition (1956). At the time we had no plans for revision of thesechapters or for any imminent extension of the Advanced book, but eventually a

plan emerged for combining a revision of the 1956 chapters with a supplementationto the 1961 book. The present book is the outcome.

Part I includes nine chapters on subjects which are necessarily specialized butwhich form important parts of the general field. Most of the topics concerned arecurrently under active investigation. In some cases the situation has changed so

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 ofrubber is transferred to Terpenoids and the chapter on Synthetic Polymers islimited to man-made elastomers, plastics, and resins, arranged according topolymerization mechanisms. Much of the chemistry of dyes is historical andremains unchanged, but modern covalently-bonded dyes were introduced lessthan a decade ago.

The sections of Part I are numbered in extension of those of Advanced for convenience in cross referencing. Thus 31.48 designates the last section of Advancedand 32.1 refers to the first section of the present book. A reference to a specificpage of the first book, e.g. 963, is entered as Adv., p. 963. A 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, R and S specification of configuration,etc.). However, most of the entries describe advances reported in the literaturesince July 1, 1961, the closing date for coverage in Advanced. We have scannedthe principal journals for papers which fit into the framework of Advanced andwhich seem to us significant and interesting, and have included in Part II accountsof the new work as supplements to the material previously published. As a checkon the accuracy of our accounts, copies for review were sent to the principal investigator of each research group involved. It is a pleasure to report that theresponse was unanimous and that the corrections and suggestions were veryhelpful. We thank the many chemists who contributed in this way to the production of an accurate survey of recent research.

We are very much indebted also to the following specialists for reviewingchapters or sections of Part I and presenting invaluable advice :

iii

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iv PREFACE

V. Boekelheide

J. A. BootheH. BrockmannC. J. W. BrooksE. ClarA. C. CopeO. C. DermerL. FarkasG. FodorR. Grewe

R. M. HerbstW. HerzC. H. HochwaltR. HuisgenI. M. HunsbergerP. KarrerR. KuhnR. V. LawrenceJ. J. LeavittE. Leete

M. D. SofterE. C. TaylorW. I. TaylorI. UgiE. E. van TamelenB. C. L. WeedonE. WenkertK. WiesnerW. C. Wildman

L. MarionM. S. NewmanW. D. OllisS. W. PelletierF. W. QuackenbushH. J. RingoldE. F. RogersT. F. SandersonH. E. SchroederA. M. Seligman

We thank Makhluf J. Haddadin and Musa Z. Nazer for careful reading of thepage proof.

The expense of preparing the many Xerox copies of manuscript that went outfor prepublication review was defrayed by a grant from Research Corporation.

New biographies are included in both Parts I and II. An asterisk is appendedto the first entry in the book of the name of a chemist whose biography appears inAdvanced Organic Chemistry. The author index provides a guide to biographiespublished in both books. References in the text throughout the book follow theprevious space-saving style of citing the date and the name of the senior author,if known to us, or of the first author listed. Part II is documented with referencesof recent date and includes authors' names as they appear in the literature; theshort-form journal abbreviations used are listed in the glossary.

The coverage of the book extends through the major journals which reached usby the date given below. Future plans depend upon the reception of Part IIof the present book. We welcome advice, as well as corrections and suggestions.Cambridge, Massachusetts Lou1s F. F1eserJanuary 1, 1963 Mary F1eser

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GLOSSARY

SOLVENTS

Al Methanol or ethanol Di Dioxane AcOH Acetic AcidAn Acetone DMF Dimethylformamide H2O WaterChf Chloroform EtOH Ethanol MeOH MethanolCgH6 Benzene Hex Hexane Py Pyridine

REAGENTS, REACTIONS

NBA N-Bromoacetamide TNM TetranitromethaneNBS N-Bromosuccinimide TsCl />-Toluenesulfonyl chlorideDNF 2,4-Dinitrofluorobenzene TsOH ^-Toluenesulfonic acidOH+ ArCO3H W.-K. Wolff-Kishner reduction

GROUPS

Ac Acetyl Cb Carbobenzoxy Phth Phthaloyl/-Bu /-Butyl Et Ethyl Ph,C Trityl, (C^3C-Bz Benzoyl Me Methyl Pr PropylCathyl Carbethoxyl Ms Mesyl, CH3SO2 Ts Tosyl, ^-CH3C6HsSO2-

Ph Phenyl

V

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vi GLOSSARY

CONSTANTS

aD Specific rotation for sodium D line at or near 250, conventionallyreported as [a]i>.

MD Molecular rotation (units, not degrees) = aD X mol. wt./lOO.X (a) Ultraviolet (UV) absorption maximum in rmi determined in

ethanol or valid for an ethanolic solution. The molecular extinction coefficient, e, or log «, is given in parentheses, (b) Infrared(IR) absorption maximum in n.

cm-1 Frequency, or wave number, of an IR absorption band.cps Cycles per sec. (nuclear magnetic resonance spectra).kcal./mole Kilogram calories per mole.

BONDS

Full line up, or to the front Wavy £, configuration unknownDotted line down, or to the rear No bond epimer mixture

SYSTEMATIC NAMES

A chemical name is divided only when each part is a correctly pronounceable wordin its own right. Examples:

1. A2-Octene (or 2-octene or octene-2). Not oct-5-ene (oct is not a word).2. A6-Cholestene-3/3-ol (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. Otherendings used as words: diene, triene, diol, polyol).

3. 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 "cholestane-3/3-ol, acetate of". The same form is appropriate for estrone acetate,cholic acid triacetate, cortisol 21-acetate.

DEVIATIONS FROM USUAL STRUCTURE

2-Desoxo- Lacking a 2-keto group3-Desoxy- Lacking a 3-hydroxyl groupHomo- (acid) —CO2H extended to —CH2CO2HNor- (acid) —CH2CH2CO2H shortened to —CH2CO2HBisnor- (acid) —CH2CH2CO2H shortened to —CO2H

SPECIFIC TO STEROIDS

7-Dehydro- 7 ,8-Olefinic derivativeD-Homo- Ring D expanded to a six-membered ringA-Nor- Ring A contracted to a five-membered ring18-Nor- Lacking the methyl group at Cn19-Nor- Lacking the methyl group at C1o

2,3-Seco- 2 ,3-Bond severed and hydrogen added at C2 and C32,3-Seco-2,3-dioic 2,3-Bond severed, C2 and C3 converted to CO2H groups

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GLOSSARY vii

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 pronunciation is stronger than with the -an equivalents. For the same reason we favordesoxo- and desoxy- over deoxo- and deoxy-.

EUROPEAN TERMS

ETH Eidgenossische Technische Hochschule, Zurich (SwissFederal Institute of Technology)

MPI Max-Planck-Institut fur Biochemie (Medizinische For-schung)

KWI Kaiser- Wilhelm-Insti tut (before World War II; now

MPI)Geheimrat Title of special academic distinction in GermanyHabilitationsschrift Independent postdoctoral research publication required

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

fessorAG. Aktiengesellschaft (Company)BASF Badische Anilin-und Soda-Fabrik (Germany)Ciba Gesellschaft fur Chemische Industrie, Basel, SwitzerlandSASM Societe d'Applications scientifique et mecaniqueUCLAF Usines chimiques des Laboratoires Francais

JOURNALS

Journal of the American Chemical SocietyAngewandte ChemieAnnalen der ChemieAnnales de chimie (Paris)Chemische Berichte (formerly Berichte der deutschen chemischen Gesellschaft)Bulletin de la societe chimique de FranceActa Chemica ScandinavicaCollection of Czechoslovak Chemical CommunicationsComptes rendus hebdomadaires des seances de l'academie des sciencesGazzetta chimica italianaHelvetica Chimica ActaJournal of the Chemical Society (London)Journal of Organic ChemistryMonatshefte fiir ChemieRecueil des travaux chimique des Pays-Bas (The Netherlands)

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viii GLOSSARY

BIOCHEMISTRY

Adenosine 9-/3-D-Ribofuranosyladenine, a nucleosideAMP Adenosine-5'-monophosphate, adenylic acid, a mononucleotideADP Adenosine-5'-diphosphate, a dinucleotideATP Adenosine-5'-triphosphate, the principal biological phosphorylat-

ing agent and repository for chemical energyDPN Diphosphopyridine nucleotide (formerly called coenzyme I), a

dinucleotide composed of AMP joined through a diphosphatelinkage to l-/3-D-ribofuranosylnicotinamide-5'-phosphate

DPNH Reduced DPNTPN Triphosphopyridine nucleotide (formerly called coenzyme II),

DPN with an additional phosphate ester group at the 2'-posi-tion in the adenosine unit

FAD Flavin adenine dinucleotide, a dinucleotide composed of AMPjoined through a diphosphate linkage to riboflavin-5'-phos-phate

FADH Reduced FADRNA Ribonucleic acid, a polymer of ribose nucleotide monophosphates

joined together by phosphate linkages between 3'- and 5'-hy-droxyl groups

DNA Desoxyribonucleic acid, a polymer of 2-desoxyribose nucleotidemonophosphates joined together by phosphate linkages between 3'- and 5'-hydroxyl groups

CoASH

UDPG

Coenzyme A, adenylic acid joined through a pyrophosphatelinkage to pantothenic acid, which is joined by a peptide linkto /3-mercaptoethanol

Uridinediphosphoglucose

Pyrimidines: Purines:

C CytosineT ThymineU Uracil

A Adenine: G Guanine

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CONTENTS

PART 1

Chapter 1

Polynuclear HydrocarbonsPhenanthrene, Structure, 3. Succinic Anhydride Synthesis, 3. Other

Synthetic Routes, 5. Addition Reactions, 6. Substitutions, 7.Oxidation, 10.

Anthracene, Structure and Reactivity, 10. Anthraquinones, Preparation and Synthesis, 14. Substitution Reactions, 16. DisplacementReactions, 18. Polyunsaturated Derivatives, 20. Reduction Products, 20.

Insect Dyes and Bacterial Pigments, 24. Cochineal-Carminic Acid,24. Kermes-Kermesic Acid, 24. Lac Dye-Laccaic Acid, 26. Rho-domycins, 26.

Polynuclear Hydrocarbons, 27. Naphthaccne, 27. Rubrene, 29.

Pentacene, Hexacene, Heptacene, 30. Chrysene, 31. 1,2-Benzan-thracene, 33. Picene, 33. Pyrene, 33. Perylene, 36. Coronene,38. Circumanthracene, 40. Hexabenzocoronene, 41. Natural Pigments, 42.

Carcinogenic Hydrocarbons, Discovery, 43. Carcinogenicity andStructure, 47. Correlation with Chemical Reactivity, 50. Synthesis, 53.

Molecular Overcrowding, 56.

Chapter 2

Aromatic Heterocyclic CompoundsFive- and Six Membered Types, 59. Furane, Pyrrole, and Thiophene,

60. Resonance, 63. Electrophilic Substitutions, 65. Diels-AlderReaction, 66. Ring Fission, 68. Pyrrole Pigments, 69. OtherTypes, 71. Indole, 72.

Triazoles and Tetrazoles, 73. Phenylpentazole, 76. TriaryltetrazoliumSalts, 77. Benzofuranes, 77. Griseofulvin, 79. Butenolides, 81.

ix

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X CONTENTS

Pyridine, Nucleophilic Substitutions and Displacements, 82. Electro-philic Substitution, Oxidation, 84. Quaternary Salts and Hydroxides, 85. Pyridine-N-Oxide, 86. Ring Fission of Pyridinium Salls,89. Production of Pyridine Derivatives, 90. Synthesis of Pyridines, 91. Quinoline and Isoquinoline, Preparation, 91. Properties,96. Dehydroquinolizinium Salts, 97.

Other Heterocycles, 98. Pteridines, 99. Sydnones, 101. Pyrones,103. Coumarins, 104. Chromane, Chromone, Xanthone, 105.

Khellin, 105. Anthocyanins, 106. Flavones and Isoflavones, 108.

Miscellaneous Pigments, 115. Ommochromes, 116. Boron Heterocycles, 117.

Chapter 3

AlkaloidsOccurrence and Isolation, 119. Degradation, 120. Pyrrolidines, 12.

Senecio Alkaloids, 121. Piperidine Derivatives, 123. The Pel-letierines, 124. Tropane Alkaloids, 127. Benzylisoquinolines, 131.

Morphine, 133. Cinchona Alkaloids, 142. Hydroisoquinolines, 142.

Ipecac Alkaloids, 143. Lupine Alkaloids, 143. Phenanthroquino-lizidines and Phenanthroindolizidines, 145. Amaryllidaceae Alkaloids, 146.

Indole Alkaloids, 147. Yohimbe Alkaloids, 151. Oxindoles, 153.

Strychnine, 154. Curare Alkaloids, 155. Ergot Alkaloids, 157.

Erythrina Alkaloids, 158. Aconite-Garrya Alkaloids, 159. Caly-canthine and Chimonanthine, 161. Alkaloid Biosynthesis, 162.

Chapter 4

TerpenoidsIsoprene Rule, 168. Terpene Hydrocarbons (C10), 169. C1o-Alcohols

and Aldehydes, 171. Monocyclic Ketones, 172. Rearrangement ofBicyclic Terpenes, 175. Camphor, 176. Cantharidin, 179.

Sesquiterpenes (Cm), Acyclic, 184. Bicyclic ds-Terpenes, 184.

Diterpenes (C20), 191. Phytol, 191. Resin Acids, 192. Sclareol Group,197. Fichtelite. 199. Cafestol, 200. Cembrene, 200. GibberellicAcid, 200.

Triterpenes (C30), 202. Squalene, 202. Polycyclic Triterpenoids, 202.

Carotenoids (C40), 205. Carotenes, 205. Lycopene, 208. cis-trans-Isomerism, 209. Bixin, 210. Crocetin, 211. Xanthophyll Alcoholsand Epoxides, 211. Ketonic Carotenoids, 212. Synthesis of Carotenoids, 215.

Biosynthesis of Terpenes, 222. Rubber, 222.

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CONTENTS

Chapter 5

Steroids 225

Sterols and Bile Acids, 225. Vitamin D, 231. Estrogens, 234. Androgens, 240. Progesterone, 244. Adrenocortical Hormones, 245.

19-Norsteroids, 251. Hormone Production, 253. Hormone Analogs, 262. Cardiac Glycosides, 265. Alkaloids, 271.

Chapter 6

Vitamins 277

Discovery, 277. Thiamine (Vitamin B1), 280. Riboflavin (VitaminB2), 282. Vitamin Bs (Pyridoxine), 284. Nicotinic Acid, 286.

Pteroylglutamic Acid, 287. Vitamin B12, 288. Pantothenic Acid,290. Biotin, 291. Vitamin A, 293. Physiological Functions ofVitamin A, 296. Tocopherols, 298. Vitamin K, 300.

Chapter 7

Chemotherapy 304Organic Arsenicals, 304. Germanin, 305. Amebicidal Drugs, 306.

Antimalarials, 307. Sulfonamides, 309. Penicillin, 313. Streptomycin, 317. Neomycins B and C, 318. Tetracyclines, 318. Chloramphenicol, 319. Macrolides, 320. AntimycinA, 324. Cycloheximideand Nonactin, 325. Polypeptide Antibiotics, 325. Actinomycin,327. Sideraminesand Sideromycins, 327. Mitomycin A, 328. OtherAntibiotics, 329. Cancer Chemotherapy, 330.

Chapter 8

Synthetic Polymers 334Polymer Types, 334. Condensation Polymerization, 335. Polyamides,

336. Polyesters, 337. Polyurethane Elastomers, 338. AdditionPolymerization of Vinyl Monomers, 339. Radical Polymerization,339. Ionic Catalysis, 340. Polyethylene, 342. Polytetrafluoro-ethylene, 342. Polystyrene, 343. Polyvinyl Halides, 344. Polyvinyl Acetate, 344. Polyacrylonitrile, 344. Polyacrylates, 345.

Stereospecific Polymerization of Olefins, 345. Copolymerization, 347.

Polymerization of Dienes, 348. Polyoxymethylene, 351.

Synthetic Resins, 351. Phenol-Formaldehyde Resins, 352. Ion-Exchange Resins, 353. Urea-Formaldehyde Resins, 353. Melamine-Formaldehyde Resins, 354. Alkyd Resins, 354. Polyester Resins,355. Epoxy Resins, 356.

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xii CONTENTS

Chapter 9

Dyes 357

Color and Constitution, 357. Direct Dyes, 358. Vat Dyeing, 360.

Mordant Dyeing, 360. Substantive Dyes, 361. Formation of Dyeon the Fiber, 362. Printing, 362.

Perkin's Mauve, 363. Rosaniline Dyes, 364. Aurin, 367. The Phthal-eins, 368. Synthetic Alizarin, 371. Polyhydroxyanthraquinones, 373.

Anthraquinone Dyes for Wool and for Hydrophobic Fibers, 374.

Synthetic Indigo, 375. Tyrian Purple, 378. Other Indigoid Dyes,378.

Indanthrone, 381. Flavanthrone, 382. Benzanthrone Dyes, 384.

Algol Colors, 387. Carbazole Types, 387. Dialkyl Dipyrazolan-thrones, 389. Dithiazolanthraquinone Dyes, 389. AnthranthroneDyes, 389. Dibenzpyrenequinones, 390. Tetracarboxyimide Dyes,390. Sulfur Dyes, 391.

Acidic and Basic Azo Dyes, 393. Substantive Azo Dyes, 396. AzoicDyes, 400. Chrome Dyes, 402. Disperse Azo Dyes, 404.

Cyanine Dyes, 405. Diazacyanines, 407. Color Photography, 410.

Reactive Dyes, 411. Brighteners, 413. Lacquer Pigments, 415.

Phthalocyanines, 415.

PART 2

(New sections alone are listed here.)

R and S Specification of Configurations, 422. Hydrogenolysis, 431. Reductionwith Diimide, 432. Trishomocyclopropenyl Cation, 448. Imidazolide Synthesisof Carbon yl Compounds, 456. Nitration of Ketones, 459. Peroxidation ofKetones, 462. Reduction of Ketones, 463. Cleavage of Phenylhydrazones andSemicarbazones, 464. Enol Ethers, 467. Reduction of a ,/3-Oxido Ketones, 478.

Phosphonate Modification of the Wittig Reaction, 482. Ethylation of Amines,486. Acetylenic Amines, 487. Liquid Ion-Exchange Systems, 489. Diazirine,493. Adamantane, 506. Twistane, 510. Optically Active Cycloalkenes andDienes, 512. Aromatic Hydrocarbons from 2-Pyrones, 519. Light-CatalyzedRearrangement of Esters, 536. Lichen Dyes, 538. Rearrangement of AllylicSulfones, 541. Oxidative Decarboxylation of Acids, 545. Alkali Cleavage of2 ,6-Dihalobenzaldehydes, 553. 2 ,3-Diphenylindenone Oxide, 554. Diaza-quinones, 556. Octaphenylcubane, 572. Pseudoaromatic Heterocycles, 578.

Synthesis of n-Rhamnose, 581. Synthesis of Arachidonic Acid, 584. ThiopheneSynthesis of Acids, 587. Vinyl Ketone Synthesis of Acids, 589. Natural Ole-finic Hydroxy Acids, 590. Distribution of Fatty Acids in Natural Glycerides, 591.

Lipids of the Honeybee, 593. Scent Attractants and Repellents of Insects, 596.

Peptide Synthesis from Acid Hvdrazides, 610. Kallidin and Bradykinin, 612.Depsipeptides, 613. Selective Chemical Cleavage of Proteins, 617.

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