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Practical organic chemistry 5ed vogel


VOGEL's
TEXTBOOK OF

PRACTICAL ORGANIC CHEMISTRY
FIFTH EDITION
Revised by former and current members of
The School of Chemistry,
Thames Polytechnic, London

Brian S. Furniss
Antony J. Hannaford
Peter W. G. Smith
Austin R. Tatchell

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Longman

Scientific &
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nice1

Copublished in the United States with
John Wiley & Sons, Inc., New York


Longman Scientific & Technical
Longman Group UK Limited
Longman House, Burnt Mill, Harlow
Essex CM20 2JE, England
and Associated Companies throughout the world

Copublished in the United States with
John Wiley & Sons, lnc., 605 Third Avenue, New York, NY 10158

© Longman Group UK Limited 1989
All rights reserved; no part of this publication
may be reproduced, stored in a retrieval system,
or transmitted in any form or by any means, electronic,
mechanical, photocopying, recording, or otherwise,
without either the prior written permission of the Publishers, or a
licence permitting restricted copying in the United Kingdom issued by
the Copyright Licensing Agency Ltd, 33-34 Alfred Place, London, WCIE 7DP.

First published 1948
New Impression with minor corrections, October 1948
Second Edition 1951
New Impression with addition of Chapter XII on Semimicro Technique 1954
Third Edition 1956
New Impression with corrections and additions 1957
New Impressions 1959, 1961, 1962, 1964, 1965, 1967
Fourth Edition 1978
Reprinted, with minor corrections 1979, 1981, 1984, 1986, 1987, 1988
Fifth Edition 1989
British Library Cataloguing in Publication Data
Vogel, Arthur Israel
Vogel's textbook of practical organic chemistry 5th ed
I. Organic chemistry. Laboratory techniques


I. Title I. Furniss, B. S. (Brian Stanley), 1941 547..'0028
ISBN 0-582-46236-3
Library of Congress Cataloging-in-Publication Data
Vogel, Arthur Israel.
Vogel's Textbook of practical organic chemistry - 5th ed. / rev.
by Brian S. Furniss ... [et al.]
p.
cm.
Fourth ed. published in 1978 under title: Vogel's Textbook of
practical organic chemistry, including qualitative organic analysis.
Includes bibliographies and indexes.
ISBN 0-470-21414-7
1. Chemistry, Organic-Laboratory manuals. 2. Chemistry,
Analytic-Qualitative. I. Furniss, Brian S. (Brian Stanley), 194111. Vogel, Arthur Israel. Vogel's Textbook of practical organic
chemistry, including qualitative organic analysis. Ill. Title.
QD26I.V63 1989
547-dc19
88-36786
CIP
Set in 10/11 pt. Lasercomp Times New Roman
Filmset by Eta Services (Typesetters) Ltd, Beccles, Suffolk
Printed in Great Britain
by The Bath Press


CONTENTS

CHAPTER 1 ORGANIC SYNTHESIS
1.1 INTRODUCTION
1.2 STRUCTURE OF THE TARGET MOLECULE
1.3 REACTION MECHANISM AND THE METHODOLOGY OF SYNTHESIS
1.4 REACTION MECHANISM AND THE STRATEGY OF SYNTHESIS
1.5 CONCLUSION

1
2
10
17
23

REFERENCES

23

CHAPTER 2 EXPERIMENTAL TECHNIOUES

26

2.1 GENERAL INSTRUCTIONS FOR SAFE WORKING IN ORGANIC CHEMICAL
LABORATORIES
2.2 PLANNING OF EXPERIMENTS AND RECORDING OF RESULTS
2.3 HAZARDS IN ORGANIC CHEMISTRY LABORATORIES
2.3.1 Introduction 34
2.3.2 Explosion and fire hazards 35
2.3.3 Reactive inorganic reagents 42
2.3.4 Hazards due to toxic chemicals 44
2.3.5 Electrical safety 51
2.3.6 Ultraviolet radiation 52
APPARATUS AND REACTION PROCEDURES
2.4 INTERCHANGEABLE GROUND GLASS JOINTS
2.5 TYPES OF GROUND GLASS JOINTS
2.6 CARE AND MAINTENANCE OF GROUND GLASS JOINTS
2.7 APPARATUS WITH INTERCHANGEABLE GROUND GLASS JOINTS
SUITABLE FOR GENERAL USE IN PREPARATIVE ORGANIC CHEMISTRY
2.8 OTHER TYPES OF INTERCHANGEABLE JOINTS AND STOPCOCKS
2.9 THE USE OF CORKS AND RUBBER STOPPERS
2.10 CUTTING AND BENDING OF GLASS TUBING

26
31
34

52
52
55
57
58
63
64
65
v


CONTENTS

2.11
2.12
2.13
2.14
2.15

GENERAL LABORATORY APPARATUS
COOLING OF REACTION MIXTURES
HEATING OF REACTION MIXTURES
MECHANICAL AGITATION
TYPICAL GROUND GLASS JOINT ASSEMBLIES FOR STANDARD
REACTION PROCEDURES
2.16 PRECAUTIONS FOR UNATTENDED REACTIONS
2.17 APPARATUS FOR SPECIAL REACTION TECHNIOUES
2.17.1
2.17.2
2.17.3
2.17.4
2.17.5
2.17.6
2.17.7
2.17.8

66
70
71
73
80
86
87

Catalytic hydrogenation 87
Reactions under pressure 97
Uncatalysed and catalysed vapour phase reactions 99
Ozonolysis 103
Organic photochemistry 106
Electrolytic (anodic) syntheses 115
Liquid ammonia techniques 116
Reactions involving air-sensitive compounds 120

ISOLATION AND PURIFICATION PROCESSES
2.18 GENERAL CONSIDERATIONS
2.19 FILTRATION TECHNIOUES
2.20 RECRYSTALLlSATlON TECHNIOUES
2.21 SUBLIMATION TECHNIOUES - FREEZE DRYING
2.22 SOLVENT EXTRACTION
2.23 DRYING OF L10UlDS OR OF SOLUTIONS OF ORGANIC COMPOUNDS IN
ORGANIC SOLVENTS
2.24 DISTILLATION AT ATMOSPHERIC PRESSURE
2.25 STEAM DISTILLATION
2.26 FRACTIONAL DISTILLATION AT ATMOSPHERIC PRESSURE
2.27 DISTILLATION UNDER DIMINISHED PRESSURE ('VACUUM' DISTILLATION)
2.28 HIGH VACUUM DISTILLATION - MOLECULAR DISTILLATION
2.29 VACUUM PUMPS
2.30 MANOMETERS, VACUSTATS, VACUUM GAUGES AND MANOSTATS
2.31 CHROMATOGRAPHY
2.32 STORAGE OF SAMPLES

165
169
171
173
181
186
191
193
197
234

DETERMINATION OF PHYSICAL CONSTANTS
2.33 MELTING POINT - MIXED MELTING POINTS
2.34 DETERMINATION OF BOILING POINT
2.35 DETERMINATION OF MOLECULAR WEIGHT
2.36 DETERMINATION OF OPTICAL ROTATORY POWER
2.37 DETERMINATION OF REFRACTIVE INDEX

236
236
241
243
244
249

REFERENCES

250

vi

131
131
133
135
153
156


CONTENTS

CHAPTER 3 SPECTROSCOPIC METHODS AND THE
INTERPRETATION OF SPECTRA

254

Introduction 254
The electromagnetic spectrum 255

3.1 INFRARED SPECTROSCOPY

256

Instrumental features of infrared spectrophotometers 258
Determination of infrared spectra 259
Sample preparation 260
Features of an infrared spectrum 268
Interpretation of an infrared spectrum 271
Characteristic group frequencies 273

3.2 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY

316

Features of the nuclear magnetic resonance spectrum 319
The chemical shift 324
Spin-spin splitting 338
Protons attached to heteroatoms 348
Simplification of IH spectra 350
Interpretation of the p.m:r, spectrum 359
Further information from 13C-spectra 360

3.3 MASS SPECTROMETRY

361

The mass spectrum 362
Appearance of the mass spectrum 372
Interpretation of the mass spectrum 373
Mass spectra of classes of organic compounds 373

14 ULTRAVIOLET-VISIBLE SPECTROSCOPY
Instrumental features of ultraviolet-visible spectrophotometers 384
Determination of ultraviolet-visible spectra 384
Laws of light absorption 385
Solvents for ultraviolet spectroscopy 386
Solution preparation 386
Optical cells and their care 387
Features of an ultraviolet-visible spectrum 388

383

REFERENCES

393

CHAPTER 4 SOLVENTS AND REAGENTS

395

4.1 THE PURIFICATION OF COMMON ORGANIC SOLVENTS

395

Saturated a1iphatic hydrocarbons 397
Aromatic hydrocarbons 398
Halogenated hydrocarbons 399
Aliphatic alcohols 400
Ethers 404
Ketones 407
Esters 409
VB


COlTEITS

Nitrogen-containing solvents 409
Sulphur-eontaining solvents 411
Phosphorus-containing solvents 412

4.2 THE PREPARATION AND PURIFICATION OF REAGENTS

413

REFERENCES

468

CHAPTER 5 ALlPHATIC COMPOUNDS

470

5.1 ALKANES

470

Structure 470
Summary ofpreparative methods and of retrosynthetic strategies 471
Spectroscopic features 472
5.1.1 The catalytic hydrogenation and chemical reduction of alkenes 472
5.1.2 The hydrolysis of alkylmagnesium halides and the
hydrogenolysis of alkyl halides and of alkyl methane- or
toluene-p-sulphonates 474
5.1.3 The reduction of aldehydes and ketones 476
5.1.4 Coupling reactions (a) using organometallic compounds, and
(b) at the anode 477

5.2 ALKENES

484

Structure 484
Summary ofpreparative methods and of retrosynthetic strategies 485
Spectroscopic features 486
5.2.1 1,2-Elimination processes (p-elimination) 486
5.2.2 The partial hydrogenation of alkynes 493
5.2.3 Wittig and related reactions 495
5.2.4 Selected rearrangements of alkynes to allenes 504

5.3 ALKYNES

507

Structure 507
Summary ofpreparative methods and of retrosynthetic strategies 508
Spectroscopic features 508
5.3.1 The dehydrogenation of vic- and gem-dihalides 509
5.3.2 The oxidation of dihydrazones of 1,2-diketones 512
5.3.3 Alkylation of a terminal alkyne 513
5.3.4 Coupling reactions leading to diynes 515

5.4 ALlPHATlC ALCOHOLS
Structure 517
Summary ofpreparative methods and of retrosynthetic strategies 517
Spectroscopic features 519
5.4.1 The reduction of aldehydes, ketones and esters 519
5.4.2 The interaction of carbonyl-containing compounds with
organometallic reagents 531
5.4.3 The hydroboration-oxidation of alkenes 542
5.4.4 The oxymercuration-demercuration of alkenes 545
5.4.5 The hydroxylation of alkenes 547
5.4.6 Methods for the protection of the hydroxyl group 550
Vlll

517


CO.TEITS

5.5 ALlPHATIC HALlDES

553

Structure 553
Summary ofpreparative methods and of retrosynthetic strategies 554
Spectroscopic features 554
5.5.1 Preparation of alkyl chlorides from alcohols 555
5.5.2 Preparation of alkyl bromides from alcohols 559
5.5.3 Preparation of alkyl iodides from alcohols 566
5.5.4 Displacement reactions involving a halogen atom 570
5.5.5 Displacement reactions involving a methanesulphonyloxy
group 572
5.5.6 Displacement reactions involving the amino group 574
5.5.7 Addition of hydrogen halides or halogens to alkenes 574
5.5.8 The replacement of reactive allylic hydrogen atoms by
bromine 577

5.6 ALlPHATIC ETHERS

579

Structure 579
Summary ofpreparative methods and of retrosynthetic strategies 580
Spectroscopic features 580
5.6.1 The formation of ethers from alcohols under acidic
conditions 581
5.6.2 The interaction of an alcohol with a halogen compound
under basic conditions 583

5.7 ALlPHATlC ALDEHYDES

585

Structure 585
Summary ofpreparative methods and of retrosynthetic strategies 585
Spectroscopic features 587
5.7.1 The controlled oxidation or dehydrogenation of primary
alcohols 587
5.7.2 The oxidative cleavage of 1,2-diols 590
5.7.3 The ozonolysis of suitably substituted alkenes 592
5.7.4 The reduction of nitrites, carboxylic acids and carboxylic
acid chlorides 594
5.7.5 Methods based upon alkyl halides 596
5.7.6 The hydrolysis and decarboxylation of ~,Il-epoxy esters
(glycidic esters) 598
5.7.7 The oxidative hydrolysis of nitronate salts derived from
primary nitroalkanes 599
5.7.8 Methods for the alkylation of the carbon chain 600

5.8 ALlPHATIC KETONES

604

Structure 604
Summary ofpreparative methods and of retrosynthetic strategies 605
Spectroscopic features 606
5.8.1 The oxidation of secondary alcohols 607
5.8.2 The hydration of alkynes 612
5.8.3 The thermal decarboxylation of acids over a metal oxide
catalyst 612
5.8.4 The interaction of organometallic compounds with
carboxylic acid chlorides and N,N-dimethylcarboxamides 616
ix


CONTENTS

5.8.5 The hydrolysis and decarboxylation of Il-keto esters and the
hydrolysis of IJ-diketones 619
5.8.6 The acid-catalysed rearrangement of 1,2-diols 623
5.8.7 The oxidative hydrolysis of nitronate salts from secondary
nitroalkanes 623
5.8.8 Methods for the protection of the carbonyl group in
aldehydes and ketones 623

5.9 DICARBONYL COMPOUNDS

626

Structure 626
5.9.1 1,2-Dicarbonyl compounds 627
5.9.2 1,3-Dicarbonyl compounds 632
5.9.3 1,4-Dicarbonyl compounds 635

5.10 CARBOHYDRATES
Structure 637
5.10.1 Carbohydrate
5.10.2 Carbohydrate
5.10.3 Carbohydrate
5.10.4 Carbohydrate
5.10.5 Carbohydrate

637
interconversions
interconversions
interconversions
interconversions
interconversions

642
644
651
658
660

5.11 ALlPHATIC CARBOXYLIC ACIDS

664

Structure 664
Summary ofpreparative methods and of retrosynthetic strategies 664
Spectroscopic features 666
5.11.1 Oxidative methods 667
5.11.2 Hydrolysis of alkyl cyanides 671
5.11.3 Carboxylation of Grignard reagents 673
5.11.4 The Arndt-Eistert method 675
5.11.5 Electrolytic (anodic) coupling 677
5.11.6 Methods utilising diethyl malonate 680
5.11.7 The synthesis of optically active carboxylic acids 687
5.11.8 Methods for the protection of the carboxyl group 690

5.12 CARBOXYLIC ACID DERIVATIVES

691

Structure 691
Summary of retrosynthetic strategies 692
Spectroscopic features 692
5.12.1 Acyl halides 692
5.12.2 Acid anhydrides 693
5.12.3 Esters 695
5.12.4 Acid amides 708

5.13 ALlPHATlC NITRILES
Summary ofpreparative methods and of retrosynthetic strategies 710
Spectroscopic features 711
5.13.1 Displacement with cyanide ion on an alkyl halide 711
5.13.2 Displacement with cyanide ion on an
arylsulphonylhydrazone 712
5.13.3 Dehydration of amides and aldoximes 715

x

710


CUIIlEITS

5.13.4 Cyanoethylation procedures and the ee-afkylatien of
nitriles 717

5.14 SUBSTITUTED CARBOXYLIC ACIDS AND THEIR DERIVATIVES

719

Structure 719
Spectroscopic features 720
5.14.1 Halogenoacids720
5.14.2 Hydroxy acids and lactones 725
5.14.3 Keto acids and esters 735
5.14.4 Amino acids and peptides 746

5.15 NITROALKANES

763

Structure 763
Summary ofpreparative methods and of retrosynthetic strategies 764
Spectroscopic features 764
5.15.1 The displacement of a halogen by a nitrite ion in an alkyl
halide 764
5.15.2 The oxidation of oximes and amines 765
5.15.3 C-Alkylation of nitroalkanes and other homologation
procedures 768

5.16 ALlPHATlC AliNES

769

Structure 769
Summary ofpreparative methods and of retrosynthetic strategies 770
Spectroscopic features 771
5.16.1 The reduction of alkyl azides, alkyl cyanides and amides 771
5.16.2 The reduction of nitro compounds and oximes 774
5.16.3 The reductive alkylation of ammonia or amines 776
5.16.4 The alkylation of ammonia and its derivatives 779
5.16.5 Imine and enamine formation 782
5.16.6 Molecular rearrangements of the Hofmann type 783
5.16.7 Methods for the protection of the amino and imino
groups 784

5.17 ALlPHATlC SULPHUR COMPOUNDS

786

Structure 786
Spectroscopic features 787
5.17.1 Thiols and thioacetals 787
5.17.2 Dialkyl sulphides (thioethers) and trialkylsulphonium
salts 789
5.17.3 Sulphoxides and suiphones 791
5.17.4 O,S-Dialkyl dithiocarbonates (xanthate esters) 792

5.18 UNSATURATED COMPOUNDS

794

5.18.1 Unsaturated alcohols 794
5.18.2 Unsaturated carbonyl compounds 798
5.18.3 Unsaturated acids and esters 820

5.19 RESOLUTION OF RACEMATES

809

REFERENCES

816

xi


COITEITS

CHAPTER 6 AROMATIC COMPOUNDS

824

6.1 AROMATIC HYDROCARBONS
Structure 824
Spectroscopic features 825
6.1.1 Alkylbenzenes 826
6.1.2 Di- and triarylmethanes 833
6.1.3 Biphenyl systems 835
6.1.4 Condensed polycyclic systems 839
6.1.5 Some non-benzenoid systems 847

824

6.2 AROMATIC NITRO COMPOUNDS
850
Summary ofpreparative methods and of retrosynthetic strategies 850
Spectroscopic features 851
6.2.1 Direct nitration 851
6.2.2 The oxidation of amines 857
6.2.3 The replacement of a diazo group by a nitro group 858
6.3 AROMATIC HALOGEN COMPOUNDS
858
Structure 858
Summary ofpreparative methods and of retrosynthetic strategies 858
Spectroscopic features 859
6.3.1 Direct halogenation 860
6.3.2 Chloromethylation 865
6.3.3 The replacement of a diazo group by a halogen 867
6.3.4 The replacement of a hydroxyl group by a halogen 867
6.3.5 Methods leading to polyvalent iodine compounds 868
6.4 AROMATIC SULPHONIC ACIDS AND THEIR DERIVATIVES
872
Structure 872
Summary ofpreparative methods and of retrosynthetic strategies 872
Spectroscopic features 873
6.4.1 Direct sulphonation 873
6.4.2 The preparation of arylsulphonyl chlorides 877
6.4.3 The preparation of arylsulphonamides 879
6.4.4 The preparation of arylsulphonate esters 883
6.4.5 Reduction products from arylsuphonyl chlorides 887
6.5 AROMATIC AliNES
888
Structure 888
Summary ofpreparative methods and of restrosynthetic strategies 889
Spectroscopic features 890
6.5.1 The reduction of nitro compounds 892
6.5.2 Molecular rearrangements of the Hofmann type 897
6.5.3 The replacement of halogen by an amino group 900
6.5.4 The replacement of a phenolic hydroxyl group by an amino
group 900
6.5.5 Alkylation and reductive alkylation procedures 901
6.5.6 Some methods for the protection of the amino and imino
groups 906
xii


CUIlEITS

6.6 SUBSTITUTION PRODUCTS OF AROMATIC AMINES

906

6.6.1 Nuclear substitution products 906
6.6.2 Acylated amines and their substitution reactions 916

6.7 FORMATION OF DIAZONIUM SALTS AND THEIR USES
6.7.1 Reactions involving replacement of the diazo group 922
6.7.2 Coupling reactions 946

920

6.8 MISCELLANEOUS AROMATIC NITROGEN COMPOUNDS
953
6.8.1 Intermediate products in the reduction of nitro compounds 953
6.8.2 Arylhydrazines 959
6.8.3 Arylureas and related compounds 963
6.9 PHENOLS AND PHENYL ETHERS
968
Summary ofpreparative methods and of retrosynthetic strategies 968
Spectroscopic features 969
6.9.1 Methods for the introduction of a hydroxyl group into an
aromatic ring 970
6.9.2 Substitution reactions of phenols 975
6.9.3 Formation of phenyl ethers 984
6.9.4 Some methods for the protection of the phenolic hydroxyl
group 988
6.10 AROMATIC ALDEHYDES
989
Summary ofpreparative methods and of retrosynthetic strategies 989
Spectroscopic features 990
6.10.1 Aromatic formylation reactions 990
6.10.2 Reactions involving modification of aromatic ring
substituents 999
6.11 AROMATIC KETONES AND OUlNONES
Summary ofpreparative methods and of retrosynthetic strategies
for aromatic ketones 1005
Spectroscopic features 1005
6.11.1 Friedel-Crafts-type acylation processes 1006
6.11.2 Synthesis of aromatic ketones from carboxylic acid
derivatives 1008
6.11.3 Quinones 1019

1005

6.12 SOME REACTIONS OF AROMATIC CARBONYL COMPOUNDS
6.12.1 The Cannizzaro reaction 1028
6.12.2 The Claisen-Schmidt and related reactions 1032
6.12.3 The Perkin and Doebner reactions 1036
6.12.4 The synthesis of diphenylpolyenes 1041
6.12.5 The benzoin condensation 1043
6.12.6 Oxime formation 1047
6.12.7 Some reactions of alkyl aryl ketones 1050
6.12.8 Methods for the protection of the aromatic carbonyl
group 1056

1028

6.13 AROMATIC CARBOXYLIC ACIDS
1056
Summary ofpreparative methods and of retrosynthetic strategies 1056
Spectroscopic features 1057
xiii


CONTENTS

6.13.1
6.13.2
6.13.3
6.13.4
6.13.5

Oxidative methods 1057
The hydrolysis of nitriles 1062
Carboxylation of the aromatic ring system 1067
Nuclear nitration of aromatic carboxylic acids and esters 1071
Some methods for the protection of the carboxyl group 1072

6.14 AROMATIC CARBOXYLIC ACID DERIVATIVES

1073

Structure 1073
Spectroscopic features 1073
6.14.1 Acid halides 1073
6.14.2 Acid anhydrides 1074
6.14.3 Esters 1076
6.14.4 Acid amides 1080

6.15 AROMATIC NITRILES

1081

Summary ofpreparative methods and of retrosynthetic strategies 1081
6.15.1 The Sandmeyer procedure 1081
6.15.2 The displacement of halogen by cyanide in an aryl halide 1082
6.15.3 The dehydration of amides and aldoximes 1082

REFERENCES

1085

CHAPTER 7 SELECTED ALICYCLIC COMPOUNDS

1087

7.1 INTRAMOLECULAR NUCLEOPHILIC DISPLACEMENT REACTIONS
7.2 INTRAMOLECULAR ADDITION REACTIONS OF CARBANIONS TO A
CARBONYL GROUP
7.3 INSERTION REACTIONS
7.4 RING EXPANSION AND RING CONTRACTION REACTIONS
7.5 REDUCTION OF AROMATIC COMPOUNDS
7.6 CYCLOADDITION REACTIONS

1087
1092
1106
1111
1114
1117

REFERENCES

1126

CHAPTER 8 SELECTED HETEROCYCLlC COMPOUNDS

1127

8.1 THREE-MEMBERED HETEROCYCLES

1127

8.1.1 Intramolecular cyclisation of a 1,2-bifunctional compound 1128
8.1.2 Insertion of a methylene group into a carbon-heteroatom
double bond 1131
8.1.3 Insertion of a heteroatom into a carbon-earbon double bond 1132
8.1.4 Heteroatom exchange 1137

8.2 FOUR-MEMBERED HETEROCYCLES
8.2.1 Cyclisation reactions 1138
8.2.2 Cycloaddition reactions 1141
XIV

1138


COlnlTS

8.3 FIVE-MEMBERED HETEROCYCLES

1144

8.3.1 Pyrroles, furans, thiophenes and pyrazolones from
dicarbonyl compounds 1146
8.3.2 Hydantoins from urea, and thiazoles from thiourea or
thioamides 1151
8.3.3 Oxazolones (and azlactones) from ex-amino acids 1155
8.3.4 Indoles, benzofurans and benzothiophenes 1156
8.3.5 Benzimidazoles and benzotriazole from o-phenylene diamine 1162

8.4 SIX-MEMBERED HETEROCYCLES
8.4.1
8.4.2
8.4.3
8.4.4
8.4.5

1164

Pyridines and pyrylium salts 1165
Pyrones and pyridones 1172
Barbituric acid and barbiturates 1174
Quinolines, isoquinolines and quinoxalines 1180
Coumarins and chromones 1190

REFERENCES

1194

CHAPTER 9 INVESTIGATION AND CHARACTERISATION OF
ORGANIC COMPOUNDS

1196

9.1 PHYSICAL CONSTANTS
9.2 THE STUDY OF SOLUBILITY BEHAVIOUR
,,3 DETECTION OF ELEMENTS PRESENT
U SPECTROSCOPIC INFORMATION
9.5 FUNCTIONAL GROUP IDENTIFICATION

1197
1198
1204
1210
1211

9.5.1 Acidic compounds 1211
9.5.2 Basic compounds 1215
9.5.3 Neutral compounds 1218

9.6 PREPARATION OF DERIVATIVES

1234

9.6.1 Saturated aliphatic hydrocarbons 1235
9.6.2 Unsaturated aliphatic hydrocarbons 1235
9.6.3 Aromatic hydrocarbons 1238
9.6.4 Alcohols and polyhydric alcohols 1241
9.6.5 Carbohydrates 1245
9.6.6 Phenols 1248
9.6.7 Enols 1251
9.6.8 Aliphatic halogen compounds 1251
9.6.9 Aromatic halogen compounds 1253
9.6.10 Aliphatic ethers 1254
9.6.11 Aromatic ethers 1255
9.6.12 Acetals 1257
9.6.13 Aldehydes and ketones 1257
9.6.14 Quinones 1261
9.6.15 Carboxylic acids 1261
9.6.16 Carboxylic acid chlorides and anhydrides 1265
9.6.17 Esters 1266
xv


CONTENTS

9.6.18
9.6.19
9.6.20
9.6.21
9.6.22
9.6.23
9.6.24
9.6.25
9.6.26
9.6.27

Primaryamides 1270
Substituted amides 1271
Nitriles 1271
Primary and secondary amines 1273
Tertiaryamines 1278
ee-Amlno acids 1279
Nitro compounds 1281
Thiols 1283
Sulphonic acids 1284
Sulphonamides 1286

9.7 SEPARATION OF MIXTURES OF ORGANIC COMPOUNDS
9.7.1
9.7.2
9.7.3
9.7.4

1287

Introduction 1287
Preliminary examination of a mixture 1290
Separation of water-insoluble mixtures 1292
Separation of water-soluble mixtures 1295

CHAPTER 10 PHYSICAL CONSTANTS OF ORGANIC
COMPOUNDS

1298

Tables of derivatives 1298
Index to tables 1298

APPENDICES
1. THE LITERATURE OF ORGANIC CHEMISTRY
2. INFRARED CORRELATION TABLES
3. NUCLEAR MAGNETIC RESONANCE CORRELATION TABLES
4. MASS SPECTROMETRY CORRELATION TABLES
5. USEFUL SOLVENT CHARACTERISTICS: HAZARD SYMBOLS
6. COMMON SYNTHONS AND THEIR REAGENT EOUlVALENTS
7. SELECTION OF MANUFACTURERS AND SUPPLIERS OF LABORATORY
APPARATUS, EOUlPMENT AND CHEMICALS
Table of atomic weights 1454
Index 1455
Reference data 1511
Abbreviations 1513

XVI

1401
1412
1423
1435
1442
1447
1451


PREFACE TO FIFTH EDITION

This is the second time that we ha ve prepared a new edition of Vogel's Textbook
ofOrganic Chemistry and it is important to reaffirm the aims set out by the late
Dr A. I. Vogel in the preface to the first edition. Thus in this new edition every
endeavour is made to retain the comprehensive character of the book, and to
ensure that it continues to be a one-volume reference text which is of value to
practising organic chemists throughout their undergraduate, postgraduate and
subsequent careers.
During the preparation of the previous (fourth) edition considerable reorganisation and rewriting of the text was necessary. This arose from the many
changes which had taken place in the practice and theory of organic chemistry
during the preceding twenty years. Among these changes were the ready availability of a much wider range of substrates and reagents; the development of a
whole host of new synthetic reagents; a greater awareness of the hazards associated with handling of organic chemicals; the routine use of chromatographic
and spectroscopic techniques; and the use of mechanistic concepts to rationalise
and predict the outcome of organic reactions. That revision included a modified
chapter on experimental techniques, which was arranged under the headings
'Apparatus and reaction procedures', 'Isolation and purification processes', and
'Determination of physical constants'. New sections were introduced on safe
working in organic laboratories, chromatography, and spectroscopic methods.
The interpretation of spectroscopic data was discussed in the reorganised
chapter entitled Qualitative Organic Analysis. The preparative chapters were
reorganised on the basis of aliphatic compounds, aromatic compounds, alicyclic
compounds, and heterocyclic compounds, and within these chapters a selection
of new synthetic methods was introduced. Following the practice adopted in
previous editions these new preparations were checked in the laboratories of the
School of Chemistry, Thames Polytechnic.
In this new (fifth) edition, in order to ensure that the book retains its relevance to current teaching of organic chemistry, we have adopted the same structure of the book since we are of the opinion that it provides a bridge between the
treatment of organic chemistry theory provided by current standard undergraduate textbooks, and the wider specialist fields of the research literature.
Furthermore, in addition to the introduction of new reagents and techniques,
the last decade has seen the development of a philosophy of organic synthesis
(the strategy of synthesis) which was just beginning to emerge during the writing
of the previous edition. It is our intention to reflect this development, since we
consider that the teaching of organic chemistry must closely integrate mechanistic theory with the strategy and methodology of synthesis.
XVII


PREFACE TO THE FIFTH EDITION

The book now commences with Chapter 1, Organic Synthesis, which reviews
the important concepts which need to be borne in mind when considering the
problem: 'how may compound X be synthesised?' The chapter discusses the
structural and stereoisomeric features of molecules, the importance of control,
selectivity and protection in organic reaction sequences, and the increasing importance of asymmetric synthesis. These topics are developed further in the subsequent text. The use of computers in organic synthesis is reviewed, and this
topic leads to a short summary of the most significant contribution to the teaching of organic synthesis of the recent decade, namely the disconnection (or synthon) approach developed by Dr S. Warren and based upon the original
concept of Professor E. J. Corey. This approach has been integrated with the
theoretical discussions on preparative procedures which precede the preparative
examples in the aliphatic and aromatic chapters. In particular the retrosynthetic
analysis of target molecules has provided a framework around which the later
alicyclic and heterocyclic chapters have been rewritten. By using this approach
we hope that undergraduates and others, who become acquainted with this
philosophy in lectures and tutorials, may find this text a useful further source of
information.
The first three sections of Chapter 2 deal with Codes of Practice and responsibility, and a summary of hazards which may be encountered in the organic
chemistry laboratory. These are intended to acquaint the student with the essential features of safe working practice, and to advise strongly on the importance
of consulting with senior members of the laboratory or the appointed safety
officer, and of consulting comprehensive specialist texts which should be readily
accessible to laboratory users. In particular the advice of safety officers should
be sought, since by virtue of their office they have available the latest information. Hazards associated with particular chemicals and procedures are noted in
the text as far as information is available. The remainder of Chapter 2, Experimental Techniques, has been up-dated on the availability of new equipment and
the applicability of new techniques. An important section on reactions involving
air-sensitive compounds has been introduced. The chromatography section now
includes the important preparative techniques of flash chromatography, dry
column flash chromatography and the 'Chrornatotron', together with a fuller
discussion on high-performance liquid chromatography.
Spectroscopic methods and the interpretation of spectra are now treated together in Chapter 3. The most significant addition to this chapter is a more
detailed coverage, with examples of spectra, of 13C_n.m.r. spectroscopy which is
considered alongside 1H-n.m.r. spectroscopy. The inclusion of detailed spectroscopic data in the preparative chapters has vastly increased the opportunities for
practise by the reader in problems relating to elucidation of structure. Thus each
functional group section in the aliphatic and aromatic chapters includes a
summarising statement of the important spectroscopic features, and many ofthe
preparations conclude with a description of key data. These spectroscopic data
are only quoted if they provide information for the student from which a definitive structural assignment may be deduced. The information is quoted in several
styles. If the spectrum (i.r., n.m.r., m.s., or u.v.-visible) is simple and straightforward the style is ofthe type 'record and interpret (assign)'. If the spectrum has
interesting interpretative features, the spectroscopic details are quoted and some
guidance is provided to assist in the elucidation of structure. If, and this is parxviii


PREFACE TO THE FIFTH EDITION

ticularly appropriate with aromatic compounds, regioisomers may be compared, these features are noted.
Chapter 4, Solvents and Reagents, has been extended to include important
new reagents including alkyllithiums, boranes and new oxidants and reductants,
which are used in subsequent chapters.
Approximately 100 new experiments have been introduced into the preparative chapters [Aliphatic (Ch. 5), Aromatic (Ch. 6), Alicyclic (Ch. 7), and Heterocyclic (Ch. 8)]. Of particular interest is the introduction of some illustrative
asymmetric syntheses, important protection methods, the use of air- and
moisture-sensitive reagents, the wider use of phase transfer reactions, silicon,
phosphorus, boron, and titanium reagents, as well as examples of important
named reactions. The procedures for these new reactions have been quoted
directly from the literature but not checked in the laboratory. The examples
have been selected on the basis of their interest, generality and importance. The
style of presentation of these new experiments is sometimes somewhat briefer
than that of those experiments retained from previous editions, but we believe
that they provide a useful introduction for the advanced student to research
methods. Many further examples of reagents and techniques have been noted in
the theoretical discussions. They have been included since they provide possible
project ideas for further investigation by advanced students. It is hoped that all
these experiments will provide suitable material for the design of a full range of
practical courses. Finally, as noted above, the theoretical discussions have been
rewritten to provide an integrated and balanced coverage of mechanisms, methodology and strategy in synthesis.
Chapter 9, Investigation and Characterisation of Organic Compounds, contains much of the chemical information and preparative methods from the
chapter previously entitled Qualitative Analysis. The emphasis of this chapter is
now on achieving an understanding of chemical behaviour in association with
spectroscopic features, and correlating this information to provide a definitive
structural elucidation. In this way we hope that the material fulfils the requirements of a range of courses which deal in this topic. The tables of physical constants (Ch. 10) remain unchanged, and the appendices have been up-dated. ,
We wish to thank Professor B. R. Currell, Ph. D., C.Chem., F.R.S.C., and Dr
J. R. Parsonage, C.Chem., F.R.S.C., former and current Heads of School of
Chemistry at Thames Polytechnic, for their interest in this project and for granting permission for the use of various facilities. We are indebted to Dr E. Vidgeon
for recording the majority of the 13C-n.m.r. spectra, and to Mr V. Kyte and Mr
J. Williams for providing information on the availability and usage of laboratory equipment. The assistance of the company representatives of very many
manufacturers of chemicals and of laboratory, spectroscopic and chromatographic equipment has been invaluable; general and specific help is noted in the
acknowledgements. We are indebted to the referees who made valuable comments on the manuscript which undoubtedly helped to improve the final text.
B.S.F.
A.J.H.
April 1988

P.W.G.S

A.R.T.

xix


PREFACE TO FIRST EDITION

The present volume is an attempt to give to students of practical organic
chemistry the benefit of some twenty years' experience in research and teaching
of the subject. The real foundations of the author's knowledge of the subject
were laid in 1925-1929 when, as a research student at the Imperial College under
the late Professor J. F. Thorpe, F.R.S., he was introduced to the methods and
experimental technique employed in a large and flourishing school of research in
organic chemistry. Since that period the author and his students have been engaged inter alia in researches on Physical Properties and Chemical Constitution
(published in the Journal of the Chemical Society) and this has involved the preparation of over a thousand pure compounds of very varied type. Many of the
new procedures and much of the specialised technique developed and employed
in these researches are incorporated in this book. Furthermore, new experiments
for the elementary student have emanated from these researches; these have
been tried out with large classes of undergraduate students over several sessions
with gratifying success and have now been included in the present textbook.
In compiling this book, the author has drawn freely from all sources of information available to him - research notes, original memoirs in scientific
journals, reference works on organic chemistry, the numerous textbooks on
practical organic chemistry, and pamphlets of manufacturers of specialised
apparatus. Whilst individual acknowledgement cannot obviously be made - in
many cases the original source has been lost track of - it is a duty and a pleasure
to place on record the debt the writer owes to all these sources. Mention must,
however, be made of Organic Syntheses, to which the reader is referred for
further details of many of the preparations described in the text.
The book opens with a chapter on the theory underlying the technique of the
chief operations of practical organic chemistry: it is considered that a proper
understanding 'of these operations cannot be achieved without a knowledge of
the appropriate theoretical principles. Chapter 11 is devoted to a detailed discussion of experimental technique; the inclusion of this subject in one chapter leads
to economy of space, particularly in the description of advanced preparations. It
is not expected that the student will employ even the major proportion of the
operations described, but a knowledge of their existence is thought desirable for
the advanced student so that he may apply them when occasion demands.
Chapters III and IV are confined to the preparation and properties of
Aliphatic Compounds and Aromatic Compounds respectively. This division,
although perhaps artificial, falls into line with the treatment in many of the existing theoretical textbooks and also with the author's own lecture courses. A short
theoretical introduction precedes the detailed preparations of the various classes
XXI


PREFACE TO THE FIRST EDITION

of organic compounds: it is recommended that these be read concurrently with
the student's lecture course and, it is hoped, that with such reading the subject
will become alive and possess real meaning. The partition of the chapters in this
manner provides the opportunity of introducing the reactions and the methods
of characterisation of the various classes of organic compounds; the foundations
of qualitative organic analysis are thus laid gradually, but many teachers may
prefer to postpone the study of this subject until a representative number of elementary preparations has been carried out by the student. The division into sections will facilitate the introduction of any scheme of instruction which the
teacher considers desirable.
Chapters V-X deal respectively with Heterocyclic and Alicyclic Compounds;
Miscellaneous Reactions; Organic Reagents in Inorganic and Organic Chemistry;
Dyestuffs, Indicators and Related Compounds; Some Physiologically-Active
Compounds; and Synthetic Polymers. Many of these preparations are of course
intended for advanced students, but a mere perusal of the experimental details of
selected preparations by those whose time for experimental-work is limited may
assist to impress them on the memory. Attention is particularly directed to the
chapter on Organic Reagents in Inorganic and Organic Chemistry. It is always a
good plan to set advanced students or adequately-trained laboratory assistants
on the preparation of those compounds which are required in the laboratory for
organic and inorganic analysis; the resulting cost is comparatively low (for
o-phenanthroline, for example, it is less than one-tenth of the commercial price)
and will serve to promote the use of these, otherwise relatively expensive,
organic reagents in the laboratory.
Chapter XI is devoted to Qualitative Organic Analysis. The subject is
dicussed in moderate detail and this, coupled with the various Sections and
Tables of Physical Constants of Organic Compounds and their Derivatives in
Chapters III and IV, will provide a satisfactory course of study in this important
branch of chemistry. No attempt that has been made to deal with Quantitative
Organic Analysis in this volume.
The textbook is intended to meet the requirements of the student of chemistry
throughout the whole of his training. Considerable detail is given in those sections of particular interest to the elementary student; in the author's opinion it is
the duty of a writer of a practical textbook to lay a secure foundation of sound
experimental technique for the beginner. The subject matter of the book is sufficiently comprehensive to permit the teacher to cover any reasonable course of
instruction. It will be observed that the scale of the preparations varies considerably; the instructor can easily adapt the preparation to a smaller scale when such
a step is necessary from considerations of cost and time or for other reasons.
Quantities ofliquid reagents are generally expressed as weights and volumes: the
latter refer to a temperature of 20 0. The book will be suitable for students preparing for the Pass and Honours (General and Special) B.Sc. of the Universities,
the A.R.I.e. and the F.R.Le. (Organic Chemistry). It will also provide an introduction to research methods in organic chemistry and, it is hoped, may serve as
an intermediate reference book for practising organic chemists.
Attention is directed to the numerous references, particularly in Chapter 11
on Experimental Technique, to firms supplying specialised apparatus. The
author has usually had first-hand experience with this apparatus and he feels
that some readers may wish to know the present source of supply and also from
whom to obtain additional information. It must be mentioned that most of the
XXll


PREFACE TO THE FIRST EDITION

specialised apparatus has been introduced to the market for the first time by the
respective firms after much development research and exhaustive tests in their
laboratories. A reference to such a firm is, in the writer's opinion, equivalent to
an original literature reference or to a book. During the last decade or two much
development work has been carried out in the laboratories of the manufacturers
of chemical apparatus (and also of industrial chemicals) and some acknowledgement of the great help rendered to practical organic chemists by these industrial
organisations is long overdue; it is certainly no exaggeration to state that they
have materially assisted the advancement of the science. A short list of the various firms is given on the next page.*
ARTHUR I. VOGEL
Woolwich Polytechnic, London, SE18
December 1946

*

In this, the 5th Edition, the list of manufacturers and suppliers is given in Appendix 7.
XXllt


ACKNOWLEDGEMENTS

We gratefully acknowledge permission to use information contained in the catalogues and brochures of many manufacturers of chemicals and laboratory
equipment. The names of these companies are noted at appropriate points in the
text, and the full addresses are quoted in Appendix 7. In particular we are grateful to the following who supplied photographs: C. V. Cook and Sons Ltd
[hydrogenation apparatus, Fig. 2.63(c)], Electrothermal Engineering Ltd [heating mantles, Fig. 2.47(a), (c) and (d)], Gallenkamp [shakers, Fig. 2.53(a) and
(b)], Jencons (Scientific) Ltd (rotary evaporator, Fig. 2.112), and Lab-Marc
[heating mantle, Fig. 2.47(b)]. Permission to reproduce from the catalogues'
new line diagrams is also acknowledged as follows: Aldrich Chemical Co. Ltd
[Figs 2.23, 2.34, 2.71, 2.74(a) and (b), 2.75, 2.115, 2.120 and 2.142], BeckmanRIIC (Figs 3.6 and 3.7), J. Bibby Science Products Ltd [Figs 2.8(d), 2.29, 2.31(a)
and (b), 2.33, 2.44 and 2.89] and T. C. Research (Fig. 2.138).
Some of the new spectroscopic data are taken from the collections of the
School of Chemistry, Thames Polytechnic, and we wish to acknowledge particularly the assistance of Dr E. Vidgeon for specifically recording the majority of
the 13C_n.m.r. spectra. We acknowledge the inclusion of other spectroscopic
data from the Sadtler Collections, Standard Infrared Spectra, Standard Ultraviolet Spectra and Standard Nuclear Magnetic Resonance Spectra, Sadtler Research Laboratories, Philadelphia, USA, and from Compilation of M ass Spectral
Data, A. Cornu and R. Massot (1966-1971), Heyden and Son Ltd in collaboration with Presses Universitaires de France.
We are grateful to the following for permission to reproduce copyright material:
American Chemical Society for two tables giving 'Schematic Representation of
Summation Bands', by C. W. Young, R. B. Duval and N. Wright in Analytical
Chemistry (1951), Vol. 23, and 'Graphical Display of Chemical Shifts for Classes
of Paraffins', by L. P. Lindemann and J. Q. Adams in Analytical Chemistry
(1971), Vol. 32 (10); Butterworths for figures giving 'Decoupled Spectrum of
Crotonaldehyde', by W. MacFarlane and R. F. M. White, from Techniques of
High Resolution Nuclear Magnetic Resonance Spectroscopy (1972); Heyden &
Son Ltd, for Figs. 1 and 2 in Organic Magnetic Resonance (1972), Vol. 4; Pergamon Press Ltd, for figures from Organic Chemistry, Applications ofN M R (1969),
by L. M. Jackman and S. Sternhell (2nd edn); Sadtler Research Laboratories for
l3C nuclear magnetic resonance spectra of anisole, benzyl alcohol and hex-I-ene;
the authors for tables taken from Principles of Organic Mass Spectroscopy, by
D. H. Williams and I. Howe; Verlag Chemie GMBH for figures by E. Breitmaier,
xxv


ACKNOWLEDGEMENTS

G. Jung and W. Voelter in Angewandte Chemie (1971), Vol. 10; John Wiley &
Son Inc for a table by R. M. Silverstein, C. G. Bassler and T. C. Merrill from
Spectroscopic Identification of Organic Compounds (1974), 3rd edn; the authors
for tables taken from Carbon-13 Nuclear Magnetic Resonance for Organic
Chemists (1972) by G. C. Levy and G. L. Nelson; Springer-Verlag for 'Notes for
Users of Beilstein' in Handbook of Organic Chemistry.
Acta Chemica Scandinavica and the Author, Dr Rolf Carlson for an extract
from article by Rolf Carlson, Asa Nilsson & Mats Stromqvist, pp.7-13 Acta
Chem. Scand. B 37 (1983).
Aldrich Chemical Co. Inc. for an extract from
'''Dry Column" Flash Chromatography' by L.M. Harwood, p.25 Aldrichimica
Actca 18 (1985). American Chemical Society for extracts from articles by H.C.
Brown p.1816 J. Am. Chem Soc. 93 (1971); J.C. Sheen an, p.1156 J. Am. Chem.
Soc. 80 (1958); modified extracts from articles by H.C. Brown, p.1245 J. Am.
Chem. Soc. 83 (1961), p.2070 J. Am. Chem. Soc. 85 (1963), p.7768 J. Am. Chem.
Soc. 96 (1974), p.1088 J. Am. Chem. Soc. 86 (1964); S. Krishnamurthy & H.C.
Brown, p.3384 J. Am. Chem. Soc. 98 (1976); A.I. Meyers et al., pp.573--4 J. Am.
Chem. Soc. 98 (1976); H. Kruizinga et al., p.5188 J. Am. Chem. Soc. 103 (1981); J.
Klein, p.3613 J. Am. Chem. Soc. 81 (1959); W.S. Wadsworth et al., p.1737 J. Am.
Chem. Soc. 83 (1961); W.H. Pirkle, p.3965 J. Am. Chem. Soc. 103 (1981); L.T.
Scott, p.6313 J. Am. Chem. Soc. 102 (1980); R. Lohrmann, p.832 J. Am. Chem.
Soc. 88 (1966); P. Gassmann et aI., pp. 7606-7 J. Am. Chem. Soc. 100 (1978);
M.E. Kuehnr et al., pp.4283, 4285 J. Am. Chem. Soc. 81 (1959); A.L. Wilds,
p.5363 J. Am. Chem. Soc. 75 (1953); G. Posner, p.5106 J. Am. Chem. Soc. 94
(1972); T. Mukaiyama, p.7508 J. Am. Chem. Soc. 96 (1974).
Copyright
American Chemical Society: extract from article by D.B. Dess et al., p.4155 J.
Org. Chem. 48 (1983); modified extracts from articles by R. Ratcliffe et aI., p.4001
J. Org. Chem. 35 (170); B.H Lipshutz, p.3934 J. Org. Chem. 49 (1984); E. Juaristi,
p.2605 J. Org. Chem. 48 (1983); D.E. Bergbreiter, p.219 J. Org. Chem. 46 (1981);
A. Wissner, p.3972 J. Org. Chem. 43 (1978); H.C. Brown, p.5068 J. Org. Chem. 47
(1982); C.A. Brown & V. Ahuja, pp.2229-30 J. Org. Chem. 38 (1973); S. Krishnamurthy, p.3064 J. Org. Chem. 41 (1976); R.O. Hutchins, p.2301 J. Org. Chem. 43
(1978); J.c. Stowell, p.561 J. Org. Chem. 41 (1976); W.E. Gore et al., p.1708 J.
Org. Chem 40 (1975); T.H. Chan et al., p.3266 J. Org. Chem. 39 (1974); R.P.
Thummel, p.304 J. Org. Chem. 42 (1977); S. Kim, Y. Moon & K.H. Ahn, p.3315
J. Org. Chem. 47 (1982); H.C. Brown et al., pp.5067, 5068 J. Org. Chem. 47
(1982); M. Miyashita et al., pp. 3773, 3774 J. Org. Chem. 42 (1977); G.A. Olah,
pp.1638, 1639 J. Org. Chem. 45 (1980); D. Horton et al., p.731 J. Org. Chem. 33
(1968); N. Komblum et al., p.4536 J. Org. Chem. 47 (1982); J. McMurry et aI.,
pp.4371, 4373 J. Org.Chem. 38 (1973); G.E. Wilson et al., p.2134 J. Org. Chem. 33
(1968); J.S. Nimitz, p.212-13 J. Org. Chem. 46 (1981); W. Wierenga et al., p.311 J.
Org. Chem. 44 (1979); N. Komblum, p.455 J. Org. Chem. 22 (1957); K.E. Gilbert,
p.660 J. Org. Chem. 44 (1979); F. Rolla, p. 4328 J. Org. Chem. 47 (1982); S.R.
Wann et aI., p.2579 J. Org. Chem. 46 (1981); H.O. House et al., p.3106 J. Org.
Chem. 39 (1974); D.R. Maudling et al., pp.2938-9 J. Org. Chem. 48 (1983); RA
Sherrer et aI., p. 2129 J. Org. Chem. 45 (1980); G. Kabalka et al., p.2387 J. Org.
Chem. 51 (1986); T. Co hen, p.2056 J. Org. Chem. 42 (1977); M.P. Doyle et al.,
pp.2429, 3497 J. Org. Chem. 42 (1977); V. Balogh, p.1341 J. Org. Chem. 36 (1971);
Z.G. Hajos & D. Parrish, pp.1614, 1619, 1620 J. Org. Chem. 39 (1974); E.C.
Friedrich, p.4641 J. Org. Chem. 50 (1985); J. Wolinsky et al., p.42 J. Org. Chem.
xxvi


ACKNOWLEDGEMENTS

30 (1965); S.J. Brois, pp. 3533--4 J. Org. Chem. 27 (1962); M.O. Brimeyer et aI.,
p.4255 J. Org. Chem. 45 (1980); T. Durst, pp.2043--4 J. Org. Chem. 35 (1970);
W.T. Brady, p.2847 J. Org. Chem. 34 (1969); W.J. Houlihan, p.4512 J. Org.
Chem. 46 (1981); J.B. Hendrickson et al., p.3345 J. Org. Chem. 48 (1983); P.T.
Izzo, p.702 J. Org. Chem. 24 (1959); G. Olah, p.1247 J. Org. Chem. 44 (1979).
Copyright American Chemical Society.
American Chemical Society and the
authors for modified extracts from articles by Prof. D.N. Harpp, p.324 J. Org.
Chem. 40 (1975); Prof. A.I. Meyers, p.895-7 J. Org. Chem. 43 (1978); Prof. K.
Sharpless, p.I924 J. Org. Chem. 51 (1986); W. Clark Still, pp.2923--4 J. Org.
Chem. 43 (1978); Prof. H.H. Wasserman, p.301O J. Org. Chem. 46 (1981). Copyright American Chemical Society.
American Chemical Society, Division of
Chemical Education for modified extract from article by E.F. Silversmith, p.645
J. Chem. Ed. 63 (1986). Copyright American Chemical Society.
The Chemical Society of Japan for modified extracts from articles by T. Sugita et al., pp.
1481-2 Chemistry Letters (1982); T. Yamada et al., p.2403 Bull. Chem. Soc.
Japan 51 (1978); S. Shiraishi et al., p.1641 Bull. Chem. Soc. Japan 57
(1984).
Council of Scientific & Industrial Research, New Delhi for a modified extract from an article by O.P. Vig et al., p.1076 Indian Journal of Chemistry
15B (1977). Marcel Dekker Inc. for modified extracts from articles by G.
Kabalka, p.278 Synthetic Communications 9 (1979); A. Rahm, p.485 Synthetic
Pergamon Press Plc for extracts from articles by
Communications 12 (1982).
A. Hulkenberg et al., p.1506 Tetrahedron Letters (1982); N. Umino, p.765 Tetrahedron Letters (1976); N.R. Ayyanger, p.1099 Tetrahedron Letters (1982); O.
Repic, p.2731 Tetrahedron Letters (1982); G.W. Fleet, p.1439 Tetrahedron
Letters (1978); modified extracts from articles by E.J. Corey, p.2649 Tetrahedron
Letters (1975); S.H. Korzeniowski, p.1872 Tetrahedron Letters (1977); T.N.
Sorrell, p.2474 Tetrahedron Letters (1978); J. Tsujf et al., p.3282 Tetrahedron 39
(1983); S.S. Jew et al., p.2340 Tetrahedron 35 (1979); A.R. Katritzky, p.29
(supplement 1) Tetrahedron 37 (1981); N.J. Cusak et al., p.2160 Tetrahedron 32
(1976); L. Ghosez, pp.627, 628, 629 Tetrahedron 27 (1971); A. McKillop, p.1381
Tetrahedron 30 (1974).
Pharmaceutical Society of Japan for modified
extracts from articles by S. Yamada, p.995 Chem. Pharm. Bull. 13 (1965); p.11423 Chem. Pharm. Bull. 11 (1963). Royal Society of Chemistry for modified
extracts from articles by A.W. Johnson, p.1015 J. Chem. Soc (1946); A. Buss & S.
Warren, pp.2311-12, 2319-20 Perkin Trans. 1 J. Chem. Soc. (1985); H.R.
Hudson, p.106-7 Perkin Trans. 1 J. Chem. Soc. (1976); D.N. Gupta et al., p.2972
Perkin Trans. 1 J. Chem. Soc. (1981); CB. Reese et al., p.1490 Perkin Trans. 1 J.
Chem. Soc. (1980); G. Barger et al., p.1820 J. Chem. Soc. (1973); M.e. Whiting,
p.1370 Perkin Trans. 1 J. Chem. Soc. (1983); R.e. Cookson, p.2448 Perkin
Trans. 1 J. Chem. Soc. (1979); S.R. Landor, p.2498 J. Chem. Soc. (1967); c.n
Maycock et al., p.1855 J. Chem. Soc. (1979); M.V. Bombala et al., p.3014 Perkin
Trans. 1 J. Chem. Soc. (1979); J. Kametani et al., p.2230 Perkin Trans. 1 J. Chem.
Soc. (1981); P.H. Bentley et al., p.2224 Perkin Trans. 1 J. Chem. Soc. (1980); G.
Casiraghi et al., p.1865 Perkin Trans. 1 J. Chem. Soc. (1981).
Societe
Francais Caise de Chemie for a translated and modified extract from an article
by R. Lombard, p.1462 BulfSoc. Chem. Fr. (1958).
Springer-Verlag Heidelberg for modified extracts from 'Notes on the use of the Beilstein Handbook of
Organic Chemistry' in Beilstein Handbook of Organic Chemistry, adapted
extract by M. & A. Bodanszky, p.20 The Practise of Peptide Synthesis
(1984). George Thieme Verlag, Stuttgart-New York and the Authors for
XXVll


ACKNOWLEDGEMENTS

extracts from articles by F. Bickelhaupt, p.721 Synthesis (1983); S. Chandrasekaran (V. Bhushan et al.), p.431 Synthesis (1984); Prof. Y.S. Cheng, p.224 Synthesis (1980); Prof. J. Villieras, p.302 Synthesis (1983); modified extracts from
articles by Prof. H.C. Brown (for N.R. De Lue), p.1l5 Synthesis (1976); Prof.
H.C. Brown, p.704 Synthesis (1979); Roberto Ballini, p.1024 Synthesis (1986);
Alexander J. Fatiadi, p.357 Synthesis (1973); Prof. Tsuneo Imamoto, p.143 Synthesis (1983); Dr C.F. Lane, p.136 Synthesis (1975); Donald G. Lee, p.462 Synthesis (1978); Shunsaku Ohta, p. 833 Synthesis (1982); Prof. C. Piechucki, p.870
Synthesis 1974);John C. Stowell, p.279 Synthesis (1984); Prof. R.S. Tewari, p.331
Synthesis (1983); Dr M.C. Venuti, p.62 Synthesis (1982).
VCH Verlagsgesellschaft mbH for translated and modified extracts from articles by E. Bamberger,
p.11l8 Chem. Ber. 52 (1919); W. Huckel, pp. 342-3 Chem. Ber. 88 (1955); E.
Salmi, p.1805 Chem. Ber. 71 (1938).
John Wiley & Sons Inc. for a modified
extract by N. Kornblum, p.133 Organic Reactions 12 (1962).
Permission for the publication herein ofSadtler Standard Spectra's (Figs. 3.51,
3.53 & 3.54) has been granted, and all rights reserved, by Sadtler Research
Laboratories, Division of Bio-Rad Laboratories Inc.

xxviii


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