The chemistry of functional groups. Supplement E: The chemistry of ethers, crown ethers, hydroxyl groups and their sulphur analogues. Part 1

1156 Pages·2016·24.39 MB·English

by  Patai S. (Ed.)

Supplement E The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues
Edited by Saul Patai
Copyright 0 1980 by John Wiley & Sons. Ltd. All rights reserved.
Supplement E
Part 1
Edited by
SAUL PATAI
The Hebrew University,J entsalem
1980
JOHN WILEY & SONS
CHIC€iESTER - NEW YORK -- BRISBANE - TORONTO
A n Interscience @ Publication
Copyright 0 1980 by John Wiley & SORSL td.
All rights reserved.
No part of this book may be reproduced by any means,
nor transmitted, nclr translated into a machine language
without the written permission of the publisher.
ISBN 0 471 27771 1 (Pt. 1)
ISBN 0 471 27772 X (Pt. 2)
ISBN 0 471 27618 9 (SET)
Typeset by Preface Ltd., Salisbury, Wiltshire.
Printed in the United States of America.
M. Bartok Department of Organic Ch?mistry, J6zsef Attila University,
Szeged, Hungary.
R. G. Bergstrom Department of Chemktry, California State University,
Hayward, California, U.S.A.
G. Bertholon Groupe de Recherches sur les PhBnols, C.N.R.S. of France
(E.R.A. 600), Universite Claude Bernard‘Lyon 1, 43 Boulevard
du 11 Novembre 1918,69621 Villeurbanne Cedex, France
E. Block Department of Chemistry, University of Missouri-St Louis,
St. Louis, Missouri 63121, U.S.A.
C. H. Bushweller Department of Chemistry, University of Vermont, Burlington,
Vermont 05405, U.S.A.
R. L. Failes Department of Chemistry, Macquarie University, New South
Wales 2 1 1 3, Australia.
P. Fischer Institut fur Organische Chemie, Biochemie und Isotopen-
forschung, Universitat Stuttgart, Stuttgart, Bundesrepublik
Deutschland.
M. H. Gianni Department of Chemistry, St Michael’s College, Winooski,
Vermont 05404, U.S.A.
I. Goldberg Institute of Chemistry, Tel-Aviv University 1390 Tel-Aviv,
G
Israel.
G. GottareIIi Faculty of Industrial Chemistry, University of Bologna, Italy.
D. A. Laidler I.C.I. Corporate Laboratory, Runcorn, England and Department
of Chemistry, University of Sheffield, England.
R. Laniartine Group de Recherches sur les PhCnols, C.N.R.S. of France
(E.R.A. 600), UniversitC Claude Bernard Lyon 1, 43 Boulevard
du 1 1 lu’ovembre 19 18, 6962 1 Villeurbanne Cedex, France.
K. L. Ling Department of Organic Chemistry, J6zsef Attila University,
Szeged, Hungary.
C. L. Liotta School of Chemistry, Georgia Institute of Technology, Atlanta,
Georgia 30332, U.S.A.
A. Moln6r Institute of Organic Chemistry, J6zsef Attila University,
Szeged, Hungary.
P. Muller DCpartement de Chimie Organique, UniversitC de Genkve,
Genhve, Suisse.
V
Vi Contributing Authors
P. Pasanen Department of Chemistry, University of Turku, SF-20500
Turku 50, Finland.
M. Perrin Laboratoire de Mintralogie-Cristallographie, C.N.R.S. of
France (E.R.A. 600) UniversitC Claude Bernard Lyon 1, 43
Boulevard du 1 1 Novembre 19 18, 6926 1 Villeurbanne Cedex,
France.
R. Perrin Group de Recherches sur les PhCnols, C.N.R.S. of France
(E.R.A. 600), UniversitC Claude Bernard Lyon 1, 43 Boulevard
du 11 Novembre 1918, 69621 Villeurbanne Cedex, France.
K. Pihlaja Department of Chemistry, University of Turku, SF-20500,
Turku 50, Finland.
J. Royer Groupe de Physique MolCculaire et Chimie Organique
Quantiques, C.N.R.S. of France (E.R.A. 600), UniversitC
Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918,
69621 Villeurbanne Cedex, France.
B. Samori Faculty of Industrial Chemistry, University of Bologna. Italy.
H.-P. Schuchmann Institut fur Strahlenchemie im Max-Planck-Institut fur
Kohlenforschung, Stiftstrasse 34-36, D-4330 Mulheim a.d.
Ruhr, West Germany.
J. S. Shapiro Department of Chemistry, Macquarie University, New South
Wales 2 11 3, Australia.
T. Shono Department of Synthetic Chemistry, Kyoto University,
Kyoto 606, Japan.
von Sonntag Institut fur Strahlenchemie im Max-Planck-Institut fur
C.
Kohlenforschung, Stiftstrasse 34-36, D-4330 Mulheim a.d.
Ruhr, West Germany.
P. J. Stang Chemistry Department, The University of Utah, Salt Lake
City, Utah 841 12, U.S.A.
V. R. Stimson Department of Physicai and Inorganic Chemistry, University
of New England, Armidale 235 1, Australia.
J. F. Stoddart I.C.I. Corporate Laboratory, Runcorn, England and Department
of Chemistry, University of Sheffield, England.
C. Van de Sande Department of Organic Chemistry, State University of Gent,
Krijgslaan, 21 7 (Block S.4), B-9000 Gent, Belgium.
Vogtle Institut fur Organische Chemie und Biochemie der Universitat,
F.
Gerhard-Domagk Strasse 1, D-5300 Bonn, West Germany.
E. Weber Institut fur Organixhe Chemie und Biochemie der Universitat,
Gerhard-Domagk Strasse 1, D-5300 Bonn, West Germany.
M. Zieliliski Institute of Chemistry, Jagiellonian University, Cracow, Poland.
The present Supplement E brings material related to the chapters which appeared in
the main volumes on The Ether Linkage (1 967), on The Hydroxyl Group (1 97 l),
and on The Tkiol Group (1974). It is characteristic of the rapid development of
organic chemistry that crown ethers, which are the subjects of the first three weighty
chapters of this volume, had not even been mentioned in the main volume on
ethers, thirteen years ago!
This volume contains several chapters dealing with sulphur analogues of alcohols
and ethers. However, the first in a set of volumes (The Chemistry of theSulphonium
Group) on various sulphur-containing groups is already in press and further volumes
of the set are being planned.
Chapters on ‘Thermochemistry’ and on ‘Cyclic sulphides’ were also planned for
this volume, but did not materialize.
Jerusalem, June 1980. SAULP ATAI
vii
The Chemistry of Functional
Preface the series
Po
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.tlie 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 moiecule, 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 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 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
Preface to the series
X
(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 alone or in conjunction with other 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 A mino 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. !f 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 volumes)
The Chemistry of the Carbonyl Group (two volumes)
The Chemistry of the Ether Linkage
The Chemistry of the Amino Group
The Chemistry of the Nitro and Nitroso Groups (two parts)
The Chemistry of Carboxylic Acids and Esters
The Chemistry of the Carbon-Nitrogen Double Bond
The Chemistry of the Cyano Group
The Chemistry of Arnides
The Chemistry of the Hydrosyl Group (two parts)
The Chemistry of the Azido Group
The Chemistry of Acyl Halides
The Cheinistry of the Carbon-Halogen Bond (two parts)
The Chemistry of Quinciioid Compounds (two parts)
The Chemistry of the Thiol Group (two parts)
The Chemistry of Amidines and Imidates
The Chemistry of the Hydruzo, Azoa nd A Z O XGr~o ups (two parts)
Preface to the series xi
The Chemistry of Cyanates and their Thio Derivatives (twop arts)
The Chemistry of Diazoniuin and Diazo Groups (twop arts)
The Chemistry of the Carbon-Carbon Triple Bond (twop arts)
Supplement A: The Chemistry of Double-bonded Functional Groups (two parts)
Supplement B: The Chemistry of Acid Derivatives (twop arts)
The Chemistry of Keteiies, Alleiies and Related Compounds (two parts)
Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and
their Sulphur Analogues (two parts)
Titles in press:
The Chemistry of the Sulphonium Group
Supplement F: The Chemistry of Amiiles, Nitroso and Nitro Groups aiid their
Derivatives
Future volumes planned include:
The Cliemistry of Peroxides
The CIi emi stry of Organo me tallic Co mpour ids
The Ckeiniitry oj Sulphur-contairlirlg Compounds
Suppleineiit C: The Cheinistry of Triple-bonded Functioxal Groups
Supplement D: The Chemistry of Halides and Pseudo-halides
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
who continues to help and advise me. The efficient and patient cooperation of
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
Jerusalem, IS R A SAUL PATAI
EL
1. Synthesis of crown ethers and analogues 1
D. A. Laidler and J. F. Stoddart
2. Crown ethers - complexes and selectivity 59
F. Vogtle and E. Weber
3. Organic transformations mediated by macrocyclic multidentate ligands 157
C. L. Liotta
4. Geometry of the ether, sulphide and hydroxyl groups and structural
chemistry of macrocylic and noncyclic polyether compounds 175
I. Goldberg
Stereodynamics of alcohols, ethers, thio ethers and related compounds 215
5.
C. 1-1. Bushweller and H. Gianni
M.
6. Chiroptical properties of alcohols, ethers, thio ethers and disulphides 279
G. Gottarelli and B. Samon'
7. The mass spectra of ethers and sulphides 299
C. C. Van de Sande
8. The electrochemistry of ethers, hydroxyl groups and their sulphur
analogues 327
T. Shono
9. Electronic structures and thermochemistry of phenols 35 1
Royer, G. Bertholon, R. Perrin, R. Lamartine and M. Perrin
J.
10. Syntheses and uses of isotopically labelled ethers and sulphides 379
M. Zieliriski
11. Gas-phase thermal decompositions of simple alcohols, thiols and
sulphides 449
R. L. Failes, S. Shapiro and V. R. Stimson
J.
12. Oxidation and reduction of alcohols and ethers 469
P. Muller
13. Oxidation and reduction of sulphides 539
E. Block
14. Oxiranes 609
M. Bart6k and K. L. Ling
15. Cyclic ethers 683
M. Bart6k
...
Xlll
xiv Co 11 ten ts
16. Dehydration of diols 72i
M. Eart6k and A. Molnir
17. Enol ethers - structure, synthesis and reactions 761
P. Fischer
18. Oxathiacyclanes: preparation, structure and reactions 821
K. Pih!aja and P. Pasanen
19. Allene oxides and related species 859
P. Stang
J.
20. Advances in the chemistry of acetals, ketals and crtho esters 85 1
R. G. Bergstrom
21. The photochemistry of saturated alcohols, ethers and acetals 903
C. von Sonntag and H.-P. Schuchmann
22. The photolysis of saturated thiols, sulphides and disulphides 923
C.v on Sonntag and H.-P Schuchmann
23. Radiation chemistry 01 ::i:ohols and ethers 935
C. von Sonntag and H.-P. Schuchmann
24. Radiation chemistry of thiols, sulphides and disulphides 97 1
C. von Sonntag and H.-P. Schuchmann
Author Index 995
Subject index 1097