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The Chemistry of the carbonyl group Volume 2 Edited by Jacob Zabicky Copyright 0 1970 by John Wiley & Sons Ltd. All rights reserved. The chemistry of %hec arbony1 group Volume 2 THE CHEMISTRY OF FUNCTIONAL GROUPS A series of advanced treatises under the general editorship of Professor Saul Palai The diemistry of alkenes (published in 2 volumes) The chemistrj of the carbonyl group (published in 2 volumes) The chemistry of the ether linkage (published) The chemistry of the amino group (published) The chemistry the niticr and nitroso groups (published in 2 parts) of The chemistry of the carboxylic acids and esters (published) The chemistry of the carbon-nitrogen double bond (published) \ c=o / The chemistry of the carbonyR group Volume 2 Edited by JACOB ZkBICKY Th Weizmann Institute of Science, Rehovoth, Israel 1970 I NTERSCI ENCE BLlSH ERS PU division of John Wiley & Sons a - - - LONDON NEW YORK SYDNEY TOROXTO First published 1970 John Wiley & Ltd. Sons All Rights Reserved. No part of this publication may be reproduccd,stored aretrieval sFtcm, in or transmitted, any form or by any mcans in electronic, mechanical photocopying, rccord- ing otherwise, without the prior written per- or mission of the Copyright owner. Library of Congrcss Catalogtie Card No. 6618177 ISBN 0 471 X 98051 Made and Printcd in Great Britain by William Clowa and Limited, London and Beccls Sons To Z. Shifmanovich Two main purposes were to be served by publishing a second volume to The Chemistry of the Curbonyl Group, namely, to include chapters which failed to materialize in the first volume, and to widen the scope of the original plan. Thus, a chapter on ‘equilibrium additions’, dealing with a group of fundamental reactions of carbonyl compounds, appears now. On the other hand, the commitment to write a chapter on the syntheses and applications of isotopically labelled carbonyl compounds re- mained, as before, unfulfilled. The topic ‘oxidations of carbonyl compounds ’ was restricted in the previous volume to the oxidation of aldehydes by the transition metals. In this volume the behaviour of many other oxidants is considered, and ketones are also included as substrates. A chapter is dedicated to ‘enolization’, one of the most widely studied organic rearrangements, which undoubtedly deserves special attention in a treatise on the carbonyl group. In the first volume a chapter dealt with the effects of ultra-violet and visible radiation on carbonyl compounds. The eflects of other types of radiation are considered here in two chapters, one on ‘ra- diation chemistry’ and one on ‘mass spectroscopy’. The latter also affords an extension to the coverage of the analytical aspects of the carbonyl group presented earlier. In most volumes in the series The Chemistry ofFunctionaZ Croups, certain classes of compounds related to the functional group under consideration are assigned separate chapters. The chemical beha- viour and properties of the ‘oxocarbons’ are treated in this volume. Owing to technical reasons this volume appeared one year later than scheduled. I would like, therefore, to express my obligation to the contribiuting authors for their forbearance of such a delay. I wish to thank Professor Saul Patai for his advice and also my wife for her encouragement and patience. The Weizmann Institute of Science Rehovoth, 1970 JACOB ZABICKY Vii The Chemistry of the Functionall Groups Preface the series $0 The series ‘The Chemistry of the Functional Groups’ is planned to cover in each volume all aspects of tlie chemistry of one of the impor- tant functional groups in organic chemistry. The emphasis is laid on the functional group treated and on the effects which it exerts on the chemical and physical properties, primarily in the immediate vicinity of the group in question, and secondarily on the behaviour of the whole molecule. For instance., the volume The Chemistry of the Ether Linkage deals with reactions in which the C-0-C group is involved, as well as with the effects of the C-0-C group on the reactions of alkyl or aryl groups connected to the ether oxygen. It is the purpose of tlie volume to give a complete coverage of all properties and reactions of ethers in as far as these depend on the presence of the ether group, but the primary subject matter is not the whole molecule, but the C-0-C functional group. A further restriction in the treatment of the various functional groups in these volumes is that material included in easily and gen- erally available secondary or tertiary sources, such as Chemical Reviews, Quarterly Reviews, Organic Reactions, various ‘Advances’ and ‘Progress’ series as well as textbooks (i.e. in books which are usually found in the chemical libraries of universities and research institutes) should not, as a rule, be repeated in detail, unless it is necessary for the balanced treatment of the subject. Therefore each of the authors is asked not to give an encyclopaedic coverage of his subject, but to concentrate on the most important recent develop- ments and mainly on material that has not been adequately covered by reviews or other secondary sources by the time of writing of the chapter, and to address himself to a reader who is assumed to be at a fairly advanced post-graduate level. With these restrictions, it is realized that no plan can be devised for a volume that would give a complzte coverage of the subject with no overlap between chapters, while at the same time preserving the read- ... Vlll Preface to thc scries iX ability of the text. The Editor set llimself the goal of attaining remonable coverage with moderate overlap, wj th a minimum of cross- references between the chapters ot’ each volume. In this manner, sufficient freedom is given to each aEthor to produce readable quasi- monographic chapters. The general plan of each volume includes the following main sections : (a) An introductory chapter dealing with the general and theo- retical aspects of the group. (b) One or more chapters dealing with the formation ef the func- tional group in question, either from groups present in the molecule, or by introducing the new group directly or indirectly. (c) Chapters describing the characterization and characteristics of the functional groups, i.e., chapter dealing with qualitative and a quantitative methods of determination including chemical and physi- cal methods, ultraviolet, infrared, nuclear magnetic resonance, and mass spectra; a chapter dealing with activating and directive effects exerted by the group and/or a chapter on the basicity, acidity or complex-forming ability of the group (if applicable). (d) Chapters on the reactions, transforniations and rearrange- ments which the functional group can undergo, either alone or in conjunction with other reagents. (e) Special topics which do not fit any of the above sections, such as photochemistry, radiation chemistry, biochemical formations and reactions. Depending on the nature of each functional group treated, these special topics may include short monographs on related func- tional groups on which no separate volume is planned (e.g. a chapter on ‘Thioketones’ is included in the volume The Chemistry of the Carbonyl Group, and a chapter on ‘ Ketenes’ is included in the volume The Chemistry of Alkenes). In other cases, certain compounds, though containing only the functional group of the title, may have special features so as to be best treated in a separate chapter, as e.g., ‘Poly- ethers ’ in The Chemistry of The Ether Linkage, or ‘Tetraaminoethylenes’ in The Chemistry of the Amino Group. This plan entails that the breadth, depth and thought-provoking I* Preface to the serics x nature of each chapter will differ with the views and inclinations of the author and the presentation will necessarily be somewhat uneven. Moreover, a serious problem is caused by authors who deliver their manuscript late or not at all. In order to overcome this problem at least to some extent, it was decided to publish certain volumes in several parts, without giving consideration to the originally planned logical order of the chzpters. If after the appearance of the originally planned parts of a volume it is found that either owing to non-delivery of chapters, or to new developments in the subject, sufficient material has accumulated for publication of an additional part, this will be done as soon as possible. The overall plan of the volumes in the series ‘The Chemistry of the Functional Groups‘ includes the titles listed below: T”ze Chemistiy of the Alkenes (published in two volumes) The Chemistry of the Carbonyl Group (published in two volumes) The Chemistry of the Ether Linkage (published) The Chemistry of the Amino Group (published) The Chemistry of tire Nitro and Nitroso Group (published in tmo parts) Thz Chemistry of Carboxylic Acids and Esters (published) The Chemistry of the Carbon-Nitrogen Double Bond (published) The Chemistry of the Cyano Group (in press) The Chemistry of the Amides (in press) The Chemistry of the Carbon-Halogen Bond (inp reparation) The Chemislry of the Hydroxyl Group (it2 press) T/ie Chenrishy of the Carbon-Carbon Triple Bond The Chemistry of the Azido Group (in preparation) The Chemistry of lniidoates and Amidines The Chcmistry of the Thiol Goup The Chemistry of the Hydrazo, Azo and hoxy Groups The Chemi:t ry of Carbonyl Halides (in preparation) The Chemistry of the SO, SO,, 4 0 , H and -SO,H Groups The Chemistry of the -OCN, -NCO and -SCN Groups The Chemistry of the -PO,H, arid Relatzd Groups Advice or criticism regarding the plan and execution of this series will be welcomed by the Editor. The publication of this series would never have started, let alone continued, without the support of many persons. First and foremost among these is Dr. Arnold Weissberger, whose reassurance and trust encouraged me to ta-cli_le this task, and who contiiues to help and Preface to the series xi advise me. The efficient and patient cooperation of several staff- mcmbers of the Publisher also rendered me invaluable aid (but un- fortunately their code of ethics does not allow me to thank them by name). Many of my friends and colleagues in Jerusalem helped me in the solution of various major and minor matters, and my thanks are due especially to Prof. Y.L iwschitz, Dr. Z. Rappoport and Dr. J. Zabicky. Caiq6ng out such a long-range project would be quite impossible without the non-professional but none the less essential participation and partnership of my wifc:. The Hebrew University, SAULP ATAI Jerusalem, ISRAEL

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