Organic Selenium and Tellurium Compounds: Volume 1 (1986)

939 Pages·1986·24.187 MB·English

The chemistry of
organic selenium and tel Iu r iu m
compounds
Volume 1
THE CHEMISTRY OF FUNCTIONAL GROUPS
A series of advanced treatises under the general editorship of
Professor Saul Patai
The chemistry of alkenes (2 volumes)
The chemistry of the carbonyl group (2 volumes]
The chemistry of the ether linkage
The chemistry of the amino group
The chemistry of the nitro and nitroso groups (2 parts)
The chemistry of carboxylic acids and esters
The chemistry of the carbon-nitrogen double bond
The chemistry of amides
The chemistry of the cyano group
The chemistry of the hydroxyl group (2 parts)
The chemistry of the azido group
The chemistry of acyl halides
The chemistry of the carbon-halogen bond (2 parts)
The chemistry of the quinonoid compounds (2 parts)
The chemistry of the thiol group (2 parts)
The chemistry of the hydrazo, azo and azoxy groups (2 parts)
The chemistry of amidines and imidates
The chemistry of cyanates and their thio derivatives (2 parts)
The chemistry of diazonium and diazo groups (2 parts)
The chemistry of the carbon-carbon triple bond (2 parts)
The chemistry of ketenes, allenes and related compounds (2 parts)
The chemistry of the sulphonium group (2 parts)
Supplement A: The chemistry of double-bonded functional groups (2 parts)
Supplement B: The chemistry of acid derivatives (2 parts)
Supplement C: The chemistry of triple-bonded functional groups (2 parts)
Supplement D: The Chemistry of halides, pseudo-halides and azides (2 parts)
Supplement E: The chemistry of ethers, crown ethers, hydroxyl groups and
their sulphur analogues (2 parts)
Supplement F: The chemistry of amino, nitroso and nitro compounds
and their derivatives (2 parts)
The chemistry of the metal-carbon bond (3 volumes)
The chemistry of peroxides
The chemistry of
organic selenium and tellurium
compounds
Volume 1
Edited by
SAULP ATAI
and
ZVI RAPPOPORT
The Hebrew University, Jerusalem
1986
JOHN WILEY & SONS
CHICHESTER - NEW YORK - BRISBANE - TORONTO - SINGAPORE
An Interscience 8 Publication
Copyright 0 1986 by John Wiley & Sons Ltd
All rights reserved.
No part of this book may be reproduced by any means, or
transmitted, or translated into a machine language without
the written permission of the publisher.
Library of Congress Cataloging-in-Publication Data:
Main entry under title:
The Chemistry of organic selenium and tellurium
compounds.
(The Chemistry of functional groups)
'An Interscience publication.'
Includes index.
I. Organoselenium compounds. 2. Organotellurium
comoounds. I. Patai. Saul. 11. Rap.P. o.p ort, Zvi.
111. Series.
QD412.SSC53 1986 547,0572 85-17868
ISBN 0 471 90425 2
British Library Cataloguing in Publication Data:
The Chemistry of Organic Selenium and tellurium
compounds.-(The Chemistry of functional groups)
VOl. I
1, Organoselenium compounds 2. Orgnnotellurium
compounds
1. Patai, Saul 11. Rappoport. Zvi. 111. Series
547.05724 QD412.S
ISBN 0 471 90425 2
Printed and bound in Great Britain
Contributing Authors
R. Badiello C. N. R., Servizio Regionale di Sicurezza del Lavoro e Protezione
Sanitaria, Facolta di Farmacia dell’Universita di Bologna, Italy
L. Batt Aberdeen University, Aberdeen. Scotland
J. Bergrnan Department of Organic Chemistry, Royal Institute of Technology,
S-10044 Stockholm, Sweden
D. Chakraborti Department of Chemistry, Texas A&M Univcrsity, College Station,
Texas 77843, USA
I. G. Csizmadia Department of Chemistry, University of Toronto, Toronto, M5S I Al,
Canada
L. Engman Department of Organic Chemistry. Royal Institute of Technology,
S-10044 Stockholm. Sweden
F. Fringuelli Dipartimento di Chimica, Universita di Perugia, Perugia, Italy
K. Fujirnori Department of Chemistry, The University of Tsukuba, Sakura-mura
Niihari-gun, Ibaraki-ken, 305 Japan
M. L. Gross Department of Chemistry, University of Nebraska, Lincoln, Neb-
raska 68588-0304, USA
H. J. Gysling Research Laboratories, Eastman Kodak Company, Rochester, New
York 14650, USA
I. Hargittai Hungarian Academy of Sciences, Research Laboratory for Inorganic
Chemistry, Department of Structural Studies, P.O. Box 117,
Budapest, H-1431, Hungary
L. Hevesi Department of Chemistry, Facultes Universitaires Notre-Dame de la
Paix, 61, Rue de Bruxelles, B-5000 Namur, Belgium
K. J. lrgolic Department of Chemistry, Texas A&M University, College Station,
Texas 71843, USA
K. A. Jensen University of Copenhagen, Chemical Laboratory 11, The H. C.$ rsted
Institute, Copenhagen, Denmark
A. K j w Department of Organic Chemistry. The Technical University of
Denmark, Lyngby, Denmark
N. P. Luthra Department of Chemistry, University of South Carolina, Columbia,
South Carolina 29208, USA
S. Oae Okayama University of Science. Ridai-cho 1-1, Okayama, 700 Japan
J. D. Odorn Department of Chemistry, University of South Carolina, Columbia,
South Carolina 29208, USA
V
vi Contributing authors
A. Ogawa Department of Applied Chemistry, Osaka University, Suita, Osaka,
Japan
Y. Okamoto Department of Chemistry, Polytechnic Institute of New York, 333 Jay
Street, Brooklyn, New York 11201, USA
R. A. Poirier Department of Chemistry, Memorial University of Newfoundland, St.
John’s Newfoundland, AIB 3x7, Canada
M. Renson Universite de Liege, Institut de Chimie, Sart-Tilman, 4000 Litge,
Belgium
B. Rozsondai Hungarian Academy of Sciences, Research Laboratory for Inorganic
Chemistry, Department of Structural Studies, P.O. Box 117,
Budapest, H-143 I, Hungary
J. Sid6n Department of Organic Chemistry, Royal Institute of Technology,
S-10044 Stockholm, Sweden
G. Snatzke Lehrstuhl fur Strukturchemie, Ruhruniversitat Bochum, POB 10 21
48, D-4630 Bochum, FRG
N. Sonoda Department of Applied Chemistry, Osaka University, Suita, Osaka,
Japan
G. D. Sturgeon Department of Chemistry, University of Nebraska, Lincoln, Neb-
raska 68588-0304, USA
A. Taticchi Dipartimento di Chimica, Universith di Perugia, Perugia, Italy
R. A. Zingaro Department of Chemistry, Texas A&M University, College Station,
Texas 77843, USA
Foreword
The present volume in ‘The Chemistry of Functional Groups’ series deals with organic
compounds containing selenium or tellurium atoms. This material falls outside the scope
of the set of four volumes in the same series, entitled ‘The Chemistry of the Metal-Carbon
Bond’ now in the process of publication.
The authors have been requested, whenever possible, to make comparisons between
analogous compounds containing the three chalcogen atoms sulphur, selenium and
tellurium.
Originally we intended to publish all chapters of the present volume simultaneously.
However, various technical problems forced us to change this plan and to publish eighteen
chapters separately and with separate author and subject indices for this volume. The
literature coverage of most chapters is up to the end of 1983, with occasional references
from 1984.
A second volume (edited by one of us, S.P.) is now already under active preparation and
will hopefully be published towards the end of 1986. The chapters it contains include: PES,
Mossbauer, UV, visible and Raman spectroscopy; synthetic methods; preparative uses;
seleno and telluro carbonyl derivatives; photochemistry; electrochemistry; H-bonding,
acidity and complex formation; biochemistry and pharmacology; insertion and extrusion
reactions; organo Se/Te halides; Se-N and Te-N bonds; Se-P, Se-As, Te-P and
Te- As bonds; semiconductors, metals and superconductors; Se/Te analogues of ethers;
SeCN and TeCN derivatives and Se/Te free radicals. Thus we hope that these two volumes
will cover all important aspects of the organic chemistry of the derivatives of selenium and
tellurium.
We will be very grateful to readers who would communicate to us mistakes, omissions
and proposals relating to this volume as well as to other volumes in the Functional Groups
series.
Jerusalem SAUL PATAI
July 1985 ZVI RAPPOPORT
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 ofthe 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 an encyclopaedic coverage of his subject, but to
concentrate on the most important recent developments 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
reusonabfe 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 determination including
chemical and physical 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, transformations and rearrangements which the func-
tional group can undergo, either alone or in conjunction with other reagents.
(e) Special topics which do not lit 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 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).I n 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 Amino
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 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 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 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 Amides
The Chemistry of the Hydroxyl Group (two parts)
The Chemistry of the Azido Group
The Chemistry of Acyl Halides
The Chemistry of the Carbon- Halogen Bond (two parts)
The Chemistry of the Quinonoid Compounds (two parts)
The Chemistry of the Thiol Group (two parts)
The Chemistry of Amidines and Imidates
The Chemistry of the Hydrazo, Azo and Azoxy Groups (two parts)
The Chemistry of Cyanates and their Thio Derioatives (two parts)
nte Chemistry of Diazonium and Diazo Groups (two parts)
The Chemistry of fhe Carbon-Carbon Triple Bond (two parts)
Preface to the series xi
Supplement A. The Chemistry of Double-bonded Functional Groups (two parts)
The Chemistry of Ketenes, Allenes and Related Compounds (two parts)
Supgleme,nt 8: The Chemistry of Acid Deriuatiues (two parts)
Supplement C: The Chemistry of Triple-Bonded Functional Groups (fwop arrs)
Supplement D: The Chemistry of Halides, Pseudo-halides and Arides (two parts)
Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur
Analogues (two parts)
The Chemistry of the Sulphoniurn Group (two parts)
Supplement F: The Chemistry of Amino,N itroso and Nitro Groups and their Deriuatiues (two
parts)
The Chemistry of the Metal-Carbon Bond (three volumes)
The Chemistry of Peroxides
The Chemistry of Organic Se and Te Compounds Vol. 1
Titles in press:
The Chemistry of Cyclopropanes
The Chemistry of Organic Se and Te Compounds Vol. 2
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. The eficient and patient
cooperation of several staff-members of the Publisher also rendered me invaluable aid (but
unfortunately their code ofethics 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 2.
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, SAUL PATAI
ISRAEL