The Hydroxyl Group 1971 - 1971 - Patai - Frontmatter PDF

The Chemistry of The Hydroxyl Group:Part 1
Edited by Saul Patai

Copyright 0 1971 by John Wiley & Sons Ltd. All rights reserved.
The chemistry of
the hydroxyl group
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1HE CHEMISTRY OF FUNCTIONAL GROUPS
A series of advanced treatises under the general editorship o j
Professor Saul Patni
The chemistry of alkenes (published in 2 volumes)
The chemistry of the carbonyl group (published in 2 volumes)
The chemistry of the ether linkage (published)
The chemistry of the amino group (published)
The chemistry of the nitro and nitroso groups (published in 2 parts)
The chemistry of the carboxylic acids and esters (published)
The chemistry of the carbon-nitrogen double bond (published)
The chemistry of amides (published)
The chemistry of the cyano group (published)
The chemistry of the hydroxyl group (published in 2 parts)
-OH
The chemistry of
LONDON - N E W YOXK - SYDNEY - TORONTO

INTERSCIENCE PUBLISHERS
a division of John Wiley & Sons
The Hebrew Uni~ersily,Jerusalem
SAULPATAT
Edited by
1971
t
First publishcd 1971 John Wiley 61 Sons Ltd.
All Rightr 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, record-
ing or otherwise, without the prior written pcr-
mission of the Copyright owmx.
Library of Congrcss Catalog C a d No. 77-1 16164
ISBN 0 471 66939 3
Made and Printed in Great Britain by

Butler & Tanner Ltd, Froine and London
SAULPATAI
The present volume of the series ‘The Chemistry of the Functional
Groups’ is again organized according to the general plan as described
Only one of the originally planned chapters did not materialize,

in the P:eface to the series, printed on the following pages.
that on ‘Oxidation and Reduction of Alcohols’.
V
Jerusalem, March 1970
The Chemistry of the Functional Groups
Preface $0 t h e series
The series ‘The Chemistry of the Fuiictional Groups’ is planned to

cover in each volume all aspects of the chcmistry 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 grz.ii; iz qiiesiioii, and secondariiy on the bchaviour of the
whole molecule. For instance. the volume The Chemistry of the Ether
Linkage deaIs 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. I t 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 piesence 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 thc vai-ious functional
groups in these volumes is that material i n c l d e d in easily and geR-
erally available secondary or tertiary sources, such 2s 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 coxentrate 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 a t 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 prcserving the read-
Vii
...
Vlll I’rcfaco to thc serics
ability of the tcxt. The Editor set himself the goal of attaining
remonahle coverage with moderate overlap, with a minimum of cross-
references between the chapters of each volume. In this manner,
sufficient frecdom 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 wPch tlic general and theo-

rctical aspects of the group.
(b) One or more chapters dealing with the formation of 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., a chaptsr dealing with qualitative and
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 01-
complex-forming ability of the group (if applicable).
(d) Chapters 011 the rezctioris, ti-ansformations 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 mzy include short monographs on related func-
tional groups on whish no separate volume is planned (e.g. a chapter
on ‘Thioketones’ is included in the volume The Chemistry of the
cal-bonyl Group, and a chapter on ‘Ketenes’ is included in the volume
The Chemistry of AIkmes). I n other rases, 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 gr The Ether Linkage, or ‘Tetraaminoethylenes’
in The Chemistry of the Amiico Group.
This plan entails that the breadth, depth and thought-provoking

Preface to the series ix
nature of each chaptcr will differ with the views and inclinations of
the author and thc presentation will nccessarily be somewhat uneven.
Moreover, a serious problem is caused by authors who deliver their
manuscript late or not at all. I n order to overcome this prqblem at
least to some extent, ii was decided to publish certain voll-lmes in
several parts, without giving consideration to the originally planned
logical order of the chapters. If after the appearance of the originally
planned parts ofa volume it is found that either owing tcj noik-delivery
of chapters, or to new developments in the subject, sufficient material
has accumulated for publication of a n 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:
The Chemistry of the Alkenes (published in two volumes)
The Chemistry of tJie Carbonyl Group (publisJied irc two volumes)
The Chemistry of the Ether Linkage (published)
The Chemistry of the Amino Group (published)
The Chemistry of the Nitro and the Nitroso Group (published in two parts)
The Chemistry of Carboxylic Acids and Esters (published)
Tlte Chemistry of thc Curion-Nitrogen Double Bond (published)
The! Chemistry of the Cyano Group (publirhed)
The Chemisty of the Amides (published)
Thc Chemistry of the Hydroxyl Group (published in two j a r i s )
The Chemistv of the Carbon-Halogen Bond (in preparation)
The Chemistry of curbonyl Halides (in preparation)
The Chemistry of the Xzido Group (in preparation)
The Chemistry of the Carbon-Carbon Triple Bond
TJie Chemistry of Imidoates and Amidiiies
TJie CJiemistry of the Thiol Group
TJie Chemist72 of the Quinonoid Cornpoutids
The Chemistiy of the Hydrazo, Azo and Azo~y Groujs
The Chemistry of Ihe SO,-SO,, -SO,H and 4 0 , H Grcups
The CJiemistry of the -OCN, -NCO and -SCN Groups
The Chemistry of the -POJI, and Relcted Groups
Advice or criticism regarding the plan and execfition 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 rcassurance and trust
encouraged me to tackle this task, and who continues to help and
x Preface to the series
advise me. The efficient and patient cooperation o,f several star-
riiembers 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 t<j Prof. Y.Liwschitz, Dr. 2. Rappoport and Dr. J.
Zabicky. Carrying out such a long-range project wculd be quite
impossible without the non-professional 5ut none the less essential
participation and partnership of my wifc.
The Hebrew University, SAULPATAI

Jerusalem, ISRAEL
Contributing authors
R. F. W. Bader McMastcr Uiiiversi ty, Ha mil ton, Ontario,

Canada.
1. R. L. Barker Brighton Collcge of Tcchnclogv, Sussex,
England.
R. A. Basson Atomic Energy Board, Pretoria, South Africa.
Hans-Dieter Becker General Electric Research and Developmcnt
Center, Schenectady, New York, U.S.A.
Geoffrey W. Brown Sir John Cass College, London, England.
kvorad Cekovid Institute of Chemistry, Technology and
Metallurgy, Belgrade, Yugoslavia.
R. Graham Cooks Kansas Statc University, Manhattan, Kan-
sas, U.S.A.
-*
S. K. Erickson University of Leiccster, Leicester, England.
H. M. Flowers T h e Weizmann Institute of Science, Reho-
voth, Israel.
Colin A. Fyfe University of Guclph, Guelph, Ontario,
Canada.
J. Gordon Hanna Connecticut Agricultural Experiment Sta-
tion, New Haven, Connecticur, U.S.A.
D. A. R. Happer University ol'Canterbury, Christchurch, Ncw
Zealand.
Alp0 Kankaanpera University of Turku, Turku, Finland.
H. Knoringer Institutc of Physical Chemistry, University of
Munich, Germany.
Henning Lund University of Aarhus, 8000 Aarhus C, Den-
mark.
Elliot N. Marvel1 Oregon State University, Corvallis, Oregon,
U.S.A.
Mihailo Lj. Mihailovif: University of Belgrade, Belgrade, Yugoslavia
Juhani Murto University of Helsinki, Helsinki, Finland.
S. Oae Osaka City University, Osaka, Japan.
xi.
..
Sl! Contributing authors
Kaievi Pihlaja University of Turku, Turku, Finland.
C. H. Rochester Nottingham University, Nottingharn, Eng-
land.
Pentti Salomaa University of Turku, Turku, Finland.
D. F. Sangster A.A.E.C. Research Establishment, Suthcr-
land, New South Wales, Australia.
J. Schadelin Justus-Liebig Universitat, 63 Giessen, Ger-
many.
U. Schmeling Justus-Licbig Universitat, 63 Giessen, Ger-
many.
H.-H. Schott Justus-Liebig Universitat, 63 Giessen, Ger-
many.
Sidney Siggia University of Massachusetts, Amherst, Massa-
chusetts, U.S.A.
Hj. Staudinger 'Tustus-Liebig Universitat, 63 Giessen, Ger-
"
many.
Thomas R. Stengie University of Massachusetts, Amberst, Massa-
chuset ts, U. S.A.
S. Tamagaki Osaka City University, Osaka, Japan.
V. Ullrich Justus-Liebig Universitat, 63 Giessen, Ger-
many.
J. Vaughan University of Canterbury, Christchurch, New
Zealand.
William Whalley Oregon State University, Corvallis, Oregon,
U.S.A.
1. Theoretical aspects of the chemistry of the hydroxyl
group 1
R. F. W. Bader
2. Nucleophilic attack by hydroxide and alkoxide ions 51
Colin A. Fyfe
3. Free radical and electrophilic hydroxylation 133
D. F. Sangster
4. Formation of hydroxyl groups via oxymetallation,
oxidation and reduction 193
I. R. L. Barker
5. Electrochemistry of the hydroxyl group 253
Henning Lund
6, Detection and determination of hydroxyl groups 295
Sidney Siggia, J . Gordon Hanna and Thomas R. Stenglc
7, Acidity and inter- and intra-molecular H-bonds 327
C.H. Rochester
8. Directing and activatina effects 393
D. A. R. Happer and J. Vaughan
9, Electrophilic attacks on the hydioxyl group 4.53
Pentti Salomaa, Alpo Kankaanpera and Kalevi Pihlaja
10. Oxidation and reduction of phenols - 505
Mihailo Lj. Mihailovid. and Zivorad CekoviC
11. Displacement of hydroxyl groups 593
Geoffrey W. Brown
12. The dehydration of alcohols 64 1
H. Knozinger
13. Uncatalysed rearrangements involving the hydroxyl
group 719
Elliot N. Marvel1 and William Whalley
14. Biological formation and reactions of the hydroxyl
group 755
S. K. Erickson, J. Schadelin, U. Schmeling, H.-H. Schott,
V. Ullrich and Hj. Staudinger
15. Syntheses and uses of 180-labelled hydroxylic
compounds 797
S. Oae and S. Tamagaki ...
xi11
xiv Conicnts
16. Photochemistry of alcohols and phenols 835
Hans-Dieter Becker
I?. The radiation chemistry of the hydroxyl group 93 7
R. A. Basson
18. Protection of the hydroxyl group 1001
H. M. Flowers
19. The mass spectra of hydroxyl compounds 1045
R. Graham Cooks
20. Hydroxide-alkoxide ion equilibria and their influence
on chcmical reactions 1087
Juhani Murto
Author index 1117
Subject index 1195

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The Chemistry of The Hydroxyl Group:Part 1

Edited by Saul Patai

LONDON - N E W YOXK - SYDNEY - TORONTO

Made and Printed in Great Britain by

Only one of the originally planned chapters did not materialize,

that on ‘Oxidation and Reduction of Alcohols’.

The series ‘The Chemistry of the Fuiictional Groups’ is planned to

(a) An introductory chapter dealing wPch tlic general and theo-

(c) Chapters describing the characterization and characteristics

(d) Chapters 011 the rezctioris, ti-ansformations and rearrange-

This plan entails that the breadth, depth and thought-provoking

The Hebrew University, SAULPATAI

R. F. W. Bader McMastcr Uiiiversi ty, Ha mil ton, Ontario,

Subject index 1195

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