The chemistry of organophosphorus compounds Vol.1 - Primary, secondary and tertiary phosphines, polyphosphines and heterocyclic organophosphorus(III) compounds

745 Pages·1990·12.68 MB·english

by  Hartle Frank R. (ed.)

The chemistry of
organophosphorus 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 volumes, 4 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 volumes, 4 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 (5 volumes)
The chemistry of peroxides
The chemistry of organic selenium and tellurium compounds (2 volumes)
The chemistry of the cyclopropyl group
The chemistry of sulphones and sulphoxides
The chemistry of organic silicon compounds (2 parts)
The chemistry of enones (2 parts)
The chemistry of sulphinic acids, esters and their derivatives
U’PDATES
The chemistry of a-haloketones, a-haloaldehydes and a-haloimines
Nitrones, nitronates and nitroxides
Crown ethers and analogs
Patai’s guide to the chemistry of functional groups-Saul Patai
-P
I
The chemistry of
organophosphorus compounds
Volume 1
Primary, secondary and tertiary phosphines, polyphosphines
and heterocyclic organophosphorus( Ill) compounds
Edited by
FRANK HARTLEY
R.
CranJield Institute of Technology
Cranfield, UK
1990
JOHN WILEY & SONS
CHICHESTER-NEW YORK-BRISBANE-TORONTO-SINGAPORE
An Interscience” Publication
Copyright 0 1990 by John Wiley & Sons Ltd
Ballins Lane, Chichester
West Sussex PO19 IUD, England
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.
Other Wiley Editorial Ofices
John Wiley & Sons, Inc., 605 Third Avenue,
New York, NY 10158-0012, USA
Jacaranda Wiley Ltd, G.P.O. Box 859, Brisbane,
Queensland 4001, Australia
John Wiley & Sons (Canada) Ltd, 22 Worcester Road,
Rexdale, Ontario M9W 1 LI, Canada
John Wiley & Sons (SEA) Pte Lid, 37 Jalan Pemimpin 05-04,
Block B, Union Industrial Building, Singapore 2057
Library of Congress Cataloging-in-Publication Data:
The Chemistry of organophosphorus compounds / edited by Frank R.
Hartley.
p. cm.-(The Chemistry of functional groups)
Includes bibliographical references.
Contents: v. 1. Primary, secondary, and tertiary phosphines,
polyphosphines, and heterocyclic organophosphorus(II1) compounds.
ISBN 0 471 92607 8 (v. 1)
1. Organophosphorus compounds. I. Hartley, F. R. 11. Series.
QD412.PlC444 1990 89-22591
547.07-dc20 CIP
British Library Cataloguing in Publication Data:
The Chemistry of organophosphorus compounds.
Vol. I. Primary, secondary and tertiary phosphines,
polyphosphines and heterocyclic organophosphorus(II1)
compounds.
1. Organic phosphorus compounds
I. Hartley, F. (Frank Robinson), 1942- 11. Series
R.
547.07
ISBN 0 471 92607 8
Typeset by Thomson Press (India) Ltd, New Delhi, India.
Printed and bound in Great Britain by Courier International Ltd, Tiptree, Essex
To
V. H., S. M. H., J.A. H., and E. J.H.
Contributing authors
Wesley G. Bentrude Department of Chemistry, University of Utah, Salt Lake
City, Utah 841 12, USA
John Chambers ADAS Slough Laboratory, London Road, Slough SL3
7HJ, UK
Manfred Dankowski Degussa AG, Geschaftsbereich Anorganische Chemie
Produkte, D-6000 Frankfurt, FRG
Declan G. Gilheany Department of Chemistry, St Patrick’s College, May-
nooth, Co. Kildare, Ireland
Frank R. Hartley Cranfield Institute of Technology, Cranfield, Bedford,
MK43 OAL
Harry R. Hudson Department of Applied Chemistry and Life Sciences,
Polytechnic of North London, Holloway Road, London
N7 8DB, UK
Alan N. Hughes Department of Chemistry, Lakehead University, Thun-
der Bay, Ontario, Canada
Henri B. Kagan Laboratoire de Synthtse Asymetrique, UA CNRS 255,
Universite Paris-Sud, 91405 Orsay, France
Klaus-Peter Langhans Fachbereich 9, Anorganische Chemie, Bergische
Universitat-GH Wuppertal, Gauss-Strasse 20, D-5600
Wuppertal-1, FRG
W. (Bill) Levason Department of Chemistry, University of Southampton,
Southampton SO9 5NH, UK
Mohd J. Maah Centre for Foundation Studies in Science, University of
Malaya, Kuala Lumpur, Malaysia
Catherine Mitchell Department of Chemistry, St Patrick’s College, May-
nooth, Co. Kildare, Ireland
vii
viii Contributing authors
John F. Nixon School of Chemistry and Molecular Sciences, University
of Sussex, Falmer, Brighton BN1 9QJ, UK
Geoffrey Pilcher Department of Chemistry, University of Manchester,
Manchester M13 9PL. UK
Nicholas R. Price ADAS Slough Laboratory, London Road, Slough SL3
7HJ, UK
Louis D. Quin Department of Chemistry, University of Massachusetts,
Lederle Graduate Research Center, Amherst, Massa-
chusetts 01003, USA
Kalathur S. V. Santhanam Chemical Physics Group, Tata Institute of Fundamental
Research, Colaba, Bombay 400005, India
Mitsuru Sasaki Laboratoire de Synthese Asymetrique, UA CNRS 255,
Universite Paris-Sud, 91405 Orsay, France
Othmar Stelzer Fachbereich 9, Anorganische Chemie, Bergische
Universitiit-GH Wuppertal, Gauss-Strasse 20, D-5600
Wuppertal-1, FRG
Paul Tordo Universite de Provence, CNRS UA 125-Boite 521, Av.
Normandie-Niemen, 13397 Marseille, France
Foreword
The Chemistry of Organophosphorus Compounds will be a multi-volume work within the
well established series of books covering The Chemistry of Functional Groups. It is
proposed to cover the extensive subject matter in four volumes.
Volume 1 covers primary, secondary and tertiary phosphines (PR,H,-,, n = 1-3),
polyphosphines [both P-C,-P and R(P),R’, n > 13 and heterocyclic
compounds containing phosphorus.
Volume 2 will cover phosphines oxides, sulphides and selenides.
Volume 3 will cover phosphonium salts, phosphonium ylides and phosphoranes.
Volume 4 will cover phosphinous, phosphonous, phosphinic and phosphonic acid
compounds and their halogen derivatives, R,PY, RPY,, R,P(X)Y and
RP(X)Y,, where Y = halogen and X = 0, S or Se.
For many years the nomenclature used in organophosphorus chemistry was extremely
frustrating with different compounds being given the same name by different authors. The
nomenclature has, however, now been rationalized and is summarized in Chapter 1,
Section IV.
In common with other volumes in The Chemistry of the Functional Groups series, the
emphasis is laid on the functional group treated and on the effects that 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. The coverage is
restricted in that material included in easily and generally available secondary or tertiary
sources, such as Chemical Reviews and 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), is not as a rule repeated in detail, unless it is necessary for the balanced
treatment of the subject. Therefore, each of the authors was asked not to give an
encyclopaedic coverage of his or her 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 or herself to a reader who is assumed to be at a fairly advanced postgraduate level.
With these restrictions, it is realised that no plan can be devised for a volume that would
give a complete coverage of the subject with no overlap between the chapters, while at the
same time preserving the readability of the text.
The publication of the Functional Group Series would never have started without the
support of many people. This volume would never have reached fruition without the
ix
X Foreword
help of Mrs Baylis, Mrs Vitale, Mr Mitchell with typing and the efficient and patient
cooperation of several staff members of the Publisher. Many of my colleagues in England,
Israel and elsewhere gave help in solving many problems, especially Professor Saul Patai,
without whose continual support and encouragement this work would never have been
attempted. Finally, that the project ever reached completion is due to the essential support
and partnership of my wife and family, amongst whom my eldest daughter provided both
moral support and chemical understanding in the more difficult areas of the subject.
Crantield, England FRANK HARTLEY
Contents
1. Introduction 1
F. R. Hartley
2. Structure and bonding in organophosphorus(ll1) compounds 9
D. G. Gilheany
3. Optically active phosphines: preparation, uses and chiroptical properties 51
H. B. Kagan and M. Sasaki
4. Electrochemistry of organophosphorus( Ill) compounds 103
K. S. V. Santhanam
5. Thermochemistry of phosphorus(ll1) compounds 127
G. Pilcher
6. ESR spectra of free radicals derived from phosphines 137
P. Tordo
7. Preparation of phosphines 151
D. G. Gilheany and C. M. Mitchell
8. The preparation and reactivity of bi- and poly-dentate phosphines with 191
P-C,-P bonding
0. Stelzer and K. P. Langhans
9. Chemistry and ligating properties of phospha-alkynes and their 255
derivatives
M. J. Maah and J. F. Nixon
10. Cyclic phosphines 295
L. D. Quin and A. N. Hughes
11. Nucleophilic reactions of phosphines 385
H. R. Hudson
12. Acid-base and hydrogen-bonding properties of phosphines 473
H. R. Hudson
13. Photochemistry of organophosphorus(ll1) compounds 489
M. Dankowski
14 Free-radical reactions of organophosphorus( Ill) compounds 531
W. G. Bentrude
xi