The chemistry of functional groups. Supplement B: The chemistry of acid derivatives. Part 1

761 Pages·34.381 MB·English

by  Patai S. (Ed.)

Supplement B The Chemistry of Acid Derivatives
Edited by Saul Patai
Copyright 0 1979 by John Wiley & Sons Ltd. All rights reserved.
Supplement B
The chemistry of
Part 1
Edited by
SAUL PATAI
The Hebrew University, Jerusalem
1979
JOHN WILEY & SONS
CMCHESTER - NEW YORK - BRISBANE - TORONTO
An Interscience G3 Publication
Copyright 0 1979 by Wiley & Sons Ltd.
John
All rights reserved.
part this book may be reproduced by any means,
No of
nor transmitted, nor translated into a machine language
without the written permission of the publisher.
Library Congress Catalog Card No. 75-6913
of
ISBN 0 471 99610 6 (Pt. 1)
ISBN 0 471 99611 4 (Pt. 2)
ISBN 0 471 99609 2 (Set)
Typeset by Preface Ltd., Salisbury, Wiltshire.
Printcd in Great Britain by Unwin Brothers Ltd.,
The Gresham kess, Old Woking, Surrey.
Contributing Authors
M. C. Baird Department of Chemistry, Queen’s University, Kingston,
Canada
G. V. Boyd Department of Chemistry, Chelsea CoUege, London, England
C. A. Bunton Department of Chemistry University of California, Santa
Barbara, California 93 106, U.S.A.
J. P. Coleman Corporate Research Department, Monsanto Company, St.
Louis, Missouri 63 166, U.S.A.
1. G. Csizmadia Department of Chemistry, University of Toronto, Toronto,
Ontario, Canada
S. Detoni University of Ljubljana, Yugoslavia
R. Foster Chemistry Department, University of Dundee, Dundee,
Scotland
0. Gal Boris KidriE Institute of Nuclear Sciences, VinEa-Belgrade,
S.
Yugoslavia
R. S. Givens Chemistry Department, The University of Kansas, Lawrence,
Kansas 66045, U.S.A.
D. Hadfi University of Ljubljana, Yugoslavia
R. H:kansson Division of Organic Chemistry 1, Chemical Centre, University
of Lund, Sweden
W. Kantlehner Fachhochschule Aalen, Aalen, Germany
C. Kozmuta Physical Institute, Technical University, Budapest, Hungary
N. Levi Chemistry Department, The University of Kansas, Lawrence,
Kansas 66045, U.S.A.
0. I. Midid Boris KidriE Institute Nuclear Sciences, VinEa-Belgrade,
of
Yugoslavia
M. A. Ogliaruso Department of Chemistry, Virginia Polytechnic Institute and
State University, Blacksburg, Virginia 2406 1, U.S.A.
M. R. Peterson Department Chemistry, University of Toronto, Toronto,
of
Ontario, Canada
W. H. Prichard The City University, London, England
J. Ratuskjl Institute of Organic Chemistry and Biochemistry,
Czechoslovak Academy of Sciences, Prague, Czechoslovakia
M. A. Robb Department of Chemistry, Queen Elizabeth College, University
of London, London, England
V
vi Contributing A uthors
L. S. Romsted Department of Chemistry, University of California, Santa
Barbara, California 93 106, U.S.A.
R. Shaw 1162 Quince Avenue, Sunnyvale, California 94087, U.S.A.
S. W. Tam Department of Chemistry Chung Chi College, The Chinese
University of Hong Kmg, Shatin, N.T., Hong
Kong
R. Taylor University of Sussex, Falmer, Brighton, U.K.
Voss Institute for Organic Chemistry and Biochemistry, University
J.
of Hamburg, Hamburg, Germany
Wolfe Department of Chemistry, Virginia Polytechnic Institute and
J. F.
State University, Blacksburg, Virginia 2406 1, U.S.A.
Most of the originally planned volumes of the series The Clietnistry of the Futzc-
tional Groups have appeared already or are in the press. The first two books of the
series, The Chemistry of Alkenes (1 964) and The Clzemistry of the Carbonyl Group
(1 966) each had a second volume published in 1970, with chapters not included in
the plans of the original volumes and others which were planned but failed to
materialize.
This book is the second of a set of supplementary volumes which should include
material on more than a single functional group. For these volumes a division into
six categories is envisaged, and supplementary volumes in each of these categories
will be published as the need arises. These volumes should include ‘missing chapters’
as well as chapters which give a unified and comparative treatment of several related
functional groups together.
The planned division is as follows:
Supplement A: The Chemistry of Double-Bonded Functional Groups (C=C;
C=O; C=N; N=N etc.).
SupplementB: The Chemistry of Acid Derivatives (COOH; COOR; CONHz etc.).
Supplement The Chemistry of Triple-Bonded Functional Groups (GC;C N ;
C:
-N ctc.).
3N
Supplerneiit D: The Chemistry of Halides and Pseudohalides (-F; -C1; -Br; -I;
-N3 ; -0CN; -NCO etc.).
Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and
their Sulphur Analogues.
Suppletnent F: The Chemistry of Amines, Nitroso and Nitro Compounds and
their Derivatives.
In the present volume, as usual, the authors have been asked to write chapters in
the nature of essay-reviews not necessarily giving extensive or encyclopaedic cover-
age of the material. Once more, not all planned chapters materialized, but we hope
that additional volumes of Supplement B will appear, when thcse gaps can be filled
together with coverage of new developments in the various fields treated.
Jerusalem, May 1979 SAUL PATAl
vii
The Chemistry of Functional Groups
Preface to the series
The series ‘The Chemistry of Functional Groups’ is planned to cover in each volume
all aspects of the chemistry of one of the important 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 the 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 generally 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 ail 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 complete coverage of the subject with no overlap between
chapters, while at the same time preserving the readability of the text. The Editor
set himself the goal of attaining reasonable coverage with moderate overlap, with a
minimum of cross-references between the chapters of each volume. In this manner,
sufficient freedom is given to each author 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 theoretical aspects of
the group.
(b) One or more chapters dealing with the formation of the functional group in
question, either from groups present in the molecule, or by introducing the new
group directly or indirectly.
ix
X Preface to the Series
(c) Chapters describing the characterization and characteristics of the functional
groups, i.e. a chapter dealing with qualitative and quantitative methods of deter-
mination including chemical and physical methods, ultraviolet, infrared, nuclear
magnetic resonance and mass spectra: a chapter dealing with activating and direc-
tive 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, transformations and rearrangements which the
functional group can undergo, either a!or?e cr in conjunction with othcr reagents.
(e) Special topics which do not fit any of the above sections, such as photo-
chemistry, radiation chemistry, biochemical formations and reactions. Depending
on the nature of each functional group treated, these special topics may include
short monographs on related functional 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. ‘Polyethers’ in The Chemistry of the Ether Linkage, or
‘Tetraaminoethylenes’ in The Chemistry of the Atnino Group.
This plan entails that the breadth, depth and thought-provoking nature of each
chapter will differ with the views and inclinations of the author and the presenta-
tion 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
chapters. 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 a supplementary
volume, containing material on related functional groups, this will be done as soon
as possible.
The overall plan of the volumes in the series ‘The Chemistry of Functional
Groups’ includes the titles listed below:
The Chemistry of Alkenes (two vo!umes)
The Chetnistry of the Carbonyl Group (two volutnes)
The Chemistry of the Ether Linkage
The Chemistry of the Amino Group
The Chemistry of the Nitro and Nitroso Group (twop arts)
The Chemistry of Carboxylic Acids and Esters
The Clietnistry of the Carbon -Nitrogen Double Bond
The Clietnistry of the Cyatio Group
The Chemistry of Aniides
The Clietnistry of the Hydroxyl Group (two parts)
The Chemistry of the Azido Group
The Chemistry of Acyl Halides
The Chemistry of the Carbon-Iialogen Bond (twop arts)
The Cliewistry of Quinorioid Cottipoutids (twop arts)
The Chemistry of the Thiol Group (two parts)
The Chetnisrr): of Amidines arid Imidates
Preface to the Series xi
The Chemistry of the Hydrazo, Azo and Azoxy Groups
The Chemistty of Cyanates atid their Thio Derivatives (two parts)
The Chemistry of Diazonium and Diazo Groups (two parts)
The Chemistry of the Carbon-Carbon Triple Bond (two parts)
Supplement A: The Chemistry of Double-bonded Functional Groups (two parts)
Supplement B: The Chemistry of Acid Derivatives (two parts)
Titles in press:
The Chemistry of Ketenes, Alletzes and Related Compounds
Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and
their Sulphur Analogues
The Chemistry of the Sulphoniuni Group
Future volumes planned include:
The Chemistry Organometallic Cotnpounds
of
The Chemistry of Sulphur-containing Compounds
Supplement C: The Chemistry of Triple-bonded Functional Groups
Supplement D: The Chemistry of Halides and Pseudo-halides
Supplement F: The Chemistry of Amines, Nitroso and Nitro Groups and their
Derivatives
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 tackle this task, and
continues to help and advise me. The efficient and patient cooperation of
who
several staff-members 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 Israel and overseas helped me in the solution of
various major and minor matters, and my thanks are due to all of them, especially
to Professor Z. Rappoport. Carrying out such a long-range project would be quite
impossible without the non-professional but none the less essential participation
and partnership of my wife.
The Hebrew University SAUL PATAJ
Jexsaiem, S A
K E L
1. Recent advances in the theoretical treatment of acid derivatives 1
I. G. Csizmadia, Peterson, C. Kozmuta and M. A. Robb
M. R.
2. Thermochemistry of acid derivatives 59
Shaw
R.
3. Chiroptical properties of acid derivatives 67
H&ansson
R.
4. Mass spectra of acid derivatives 121
Tam
S. W.
5. Complexes of acid anhydrides 175
Foster
R.
6. Hydrogen bonding in carboxylic acids and derivatives 21
3
D. HadZi and S. Detoni
7. The synthesis of carboxylic acids and esters and their derivatives 267
A. Ogliaruso and F. Wolfe
M. J.
8. The chemistry of lactones and lactams 49 1
G. Boyd
V.
9. The chemistry of orthoamides of carboxylic acids and carbonic acid 533
W. Kantlehner
10. Detection and determination of acid derivatives 60 1
W. H. Prichard
11. The photochemistry of organic acids, esters, anhydrides, lactones and
imides 64 1
S. Givens and Levi
R. N.
12. Radiation chemistry of acids, esters, anhydrides, lactones and lactams 755
0. I. MiCiC: and 0. S. Gal
13. The electrochemistry of carboxylic acids and derivatives: cathodic reduc-
tions 781
P. Coleman
J.
14. Decarbonylation reactions of acid halides and aldehydes by chlorotris-
(tripheny1phosphine)rhodium (I) 825
C. Raird
M.
15. Pyrolysis of acids and their derivatives 859
R. Taylor
xiii
xiv Con ten ts
16. Transcarboxylation reactions of salts of arumatic carboxylic acids 915
Ratuskjl
J.
1'7. Micellar effects upon deacylation 945
C. A. Bunton and L. S. Romsted
18. The chemistry of thio acid derivatives 1021
J. Voss
19. The synthesis of lactones and lactams 1063
J. F. !"lo!fi arid A. Ggiiaruso
M.
Author Index 1331
Subject Index 1431