General and Synthetic Methods Vol. 3 A review of the literature published during 1978 PDF
Preview General and Synthetic Methods Vol. 3 A review of the literature published during 1978
General and Synthetic Methods Volume 3 A Specialist Periodical Report General and Synthetic Methods Volume 3 A Review of the Literature Pub ished during 1978 Senior Reporter G. Pattenden, Department of Chemistry, University of Nottingham Reporters K. Cooper, University of Nottingham A. B. Holmes, University of Cambridge D. C. Howell, Lilly Research Centre, Windlesham, Surrey M. G. Hutchings, I.C.I. Organics, Manchester R. C. F. Jones, University of Nottingham G. Kneen, Wellcome Research Laboratories, Beckenham, Kent D. W. Knight, University College, Cardiff M. Mellor, Bush Boake Allen Ltd., London S. M. Roberts, University of Salford W. J. Ross, Lilly Research Centre, Windlesham, Surrey D. J. Thompson, /.C./. Organics, Manchester S. Turner, Polytechnic of North London The Chemical Society Burlington House, London, WIV OBN British Library Cataloguing in Publication Data General and synthetic methods.- (Chemical Society. Specialist periodical reports). VOl. 3 1. Chemistry, Organic-Synthesis I. Pattenden, Gerald 11. Series 547l.2 QD262 ISBN 0-85186-730-8 ISSN 0141-2140 Copyright @ 1980 The Chemical Society All Rights Reserved No part of this book may be reproduced or transmitted in any form or by any means -graphic, electronic, including photocopying, recording, taping or information storage and retrieval systems - without written permission from The Chemical Society Set in Times on Linotron and printed offset by J. W. Arrowsmith Ltd., Bristol, England Made in Great Britain In trod uc ti0 n This report on General and Synthetic Methods is similar in scope and format to the previous two volumes in the series. Developments in the synthesis of saturated heterocycles, unfortunately omitted from Volume 2, are covered in this volume (Chapter 8), and a special report on ‘Photochemistry in Synthesis’ (Chapter 10) is included. There have been several high points in synthesis during 1978, but perhaps one should use this opportunity to single out the achievements of one chemist, the illustrious E. J. Corey, who during 1978 reported first total syntheses of gib- berellic acid, the plant growth regulator (Chapter 7, ref. l),e rythronolide B, the aglycone of the erythromycin B family of antibiotics (Chapter 9, ref. 17)’ and of N-methylmaysenine, one of the antitumoural maytensenoids (Chapter 9, ref. 23), each a major achievement in synthesis design and execution. July 1979 G. PATTENDEN Cont ents Chapter 1 Saturated and Unsaturated Acyclic Hydrocarbons 1 By D. C. Horwell 1 Introduction 1 2 Saturated Hydrocarbons 2 3 Olefinic Hydrocarbons 4 4 Conjugated 1,3-Dienes 19 5 1,4-, 1,5, and 1,6-Dienes 24 6 Allenic Hydrocarbons 27 7 Acetylenic Hydrocarbons 29 8 Enynes and Polyunsaturated Hydrocarbons 32 Chapter 2 Aldehydes and Ketones 36 By.S . M. Roberts 1 Preparations of Aldehydes and Ketones 36 By Oxidation of Alcohols 36 Thio- and Seleno-ketones 37 Cyclic Ketones 37 Dicarbonyl Compounds 39 Other Preparations 41 2 Reactions of Aldehydes and Ketones 46 Alkylation 46 Aldol Reactions 48 Reduction 49 General Reactions 50 3 Preparations of Unsaturated Aldehydes and Ketones 54 4 Reactions of Unsaturated Aldehydes and Ketones 60 Alkylation 60 vii ... Vlll General and Synthetic Methods Reduction 61 Conj ugate Addition 62 General Reactions 65 5 Protected Aldehydes and Ketones 66 Preparation 66 Regeneration of Aldehydes and Ketones 67 Reactions 68 6 Halogeno-derivatives 71 Preparation 71 Reactions 72 7 Acyl, Homoenolate, Acylvinyl, and Dienolate Anion Equivalents 73 Chapter 3 Carboxylic Acids and Derivatives 75 By D. W. Knight 1 Introduction 75 2 Carboxylic Acids 75 General Synthesis 75 Diacids 77 Hydroxy- acids 77 Keto-acids 78 Unsaturated Acids 80 Decarboxylation 83 Protection and Deprotection 84 3 Lactones 85 /3-Lactones 85 Butyrolactones 86 Butenolides and Tetronic Acids 89 -Methylenebutyrolactones 93 LY Valerolactones 96 4 Macrolides 98 5 Esters 100 Esterification 100 General Synthesis 101 Diesters 104 Hydroxy- esters 106 Keto-esters 107 Unsaturated Esters 109 Thioesters and Related Compounds 114 6 Carboxylic Acid Amides 117 Synthesis 117 Reactions 120
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