The chemistry of the metal-carbon bond. V.3. Carbon-carbon bond formation using organometallic compounds

491 Pages·10.57 MB·english

by  Hartley F.R.

Thc Chemistry of the Metal--Carbon Bond, 1/01, 3
Edited by F. R. Harlley and S. Patai
Q 1985 John Wiley & Sons Ltd.
The chemistry of t h e
eta!-carbon bond
Volume
3
Carbon-carbon bond
formation using
organometallic compounds
Edited by
FRANK R. HARTLEY
The Royal Military College of Science
Shivenham, England
and
SAUL PATAT
The Hebrew University
Jerusalem, Israel
I985
JOHN WILEY & SONS
CHICHESTER - NEW YORK - BRISBANE - TORONTO - SINGAPORE
An Interscience 0 Publication
Copyright 0 1985 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 languagc without the
written permission of the publisher.
Library of Congress Cataloging in Publication Data:
Main entry under title:
Carbon-carbon bond formation using organometallic
compounds.
(The Chemistry of the metal-carbon bond; v. 3)
(The Chemistry of functional groups)
‘An Interscience publication.’
Includes indcxes.
1. Organometallic compounds. 2. Chemical bonds.
I. Hartley, F. R. 11. Patai, Saul. 111. Series.
IV. Series: Chemistry of functional groups.
QD410.C43 1984 VO~.3 547’.05~ 84-13078
[QD4111 [547’.05]
ISBN 0 471 90557 7
British Library Cataloguing in Publication Data:
The Chemistry of the metal-carbon bond.-
(The chemistry of functional groups)
Vol. 3: Carbon-carbon bond formation using
organometallic compounds
1. Organometallic compounds
I. Hartley, Frank 11. Patai, Saul
547‘.05 QD41 I
ISBN 0 471 90557 7
Photoset by Thomson Press (India) Ltd., and printed and
bound in Great Britain a1 The Bath Press. Avon
Volume %--Contributing authors
Gordon K. Anderson Departincnt of Chemistry, University of Missouri-St. Louis,
St. Louis. Missouri 63121, USA
G. Paolo Chiusoli Istituto di Chimica Organica dcll’Universiti, Via M. D’Azeglio
85, 43100 Parma, Italy
Chit-Kay Chu Chemistry Department, University of Malaya, Kuala Lumpur
22- 1 1, Malaysia
V. G. Kurnar Das Chemistry Department, University of Malaya, Kuala Lumpur
22- 1 1, Malaysia
Julian A. Davies Department of Chemistry, College of Arts and Sciences,
University of Toledo, Toledo, Ohio 43606, USA
Donald M. Fenton Science and Technology Division, Union Oil Company of
California, P.O. Box 76, Brea, California 92621, USA
G. Henrici-Olive Department of Chemistry, University of California at San
Diego, San Diego, California, USA
Jon E. Johansen Division of Applied Chemistry, SINTEF, N-7034 Trondheim-
NTH, Norway
Leone Miginiac Laboratoirc de Synthese Organique, Universite de Poitiers, 40
Avenuc du Recteur Pincau, 86022 Poiticrs, France
Eric L. Moorehead Science and Technology Division, Union Oil Company of
California, P.O. Box 76, Brea, California 92621, USA
S. Olive Department of Chemistry, University of California at San
Diego, San Diego, California, USA
Olav-T. Onsager Laboratory of Industrial Chemistry, Norwegian Institutc of
Technology, University of Trondheim, N-7034 Trondheim-
NTH, Norway
Giaseppe Salerno Dipartimento di Chimica, Univcrsili dcila Calabria, Arcava-
cata di Rendc, Coscnza, Italy
Furnie Sat0 Department of Chemical Engineering, Tokyo Institute of
Technology, Meguro, Tokyo 152, Japan
V
vi Volume 3-contributing authors
Randy J. Shaver Department of Chemistry, College of Arts and Sciences,
University of Toledo, Toledo, Ohio 43606, USA
Jiro Tsuji Department of Chemical Engineering, Tokyo Institute of
Technology, Meguro, Tokyo 152, Japan
Mark J. Winter Department of Chemistry, The Univcrsity, Sheffield S3 7HF,
UK
Foreword
The Chemistry of the Metal-Carbon Bond is a multi-volume work within the weli
established series of books covering The Chemistry of Functional Groups. It aims to cover
the chemistry of the metal-carbon bond as a wholc, but lays emphasis on the carbon end.
It should therefore be of particular interest to the organic chemist. The general plan ofthc
material will be thc same as in previous books in the serics with the exception that, because
of the large amount of material involved, this will be a multi-volume work.
The first volume was conccrncd with:
(a) Thc structure and thermochemistry of organomctallic compounds.
(b) Thc preparation of organometallic compounds.
(c) The analysis and spectroscopic characterization of organometallic compounds.
The sccond volunic was conccrncd with cleavage of the nietal-carbon bond. insertions
into metal-carbon bonds, nucleophilic and clcctrophilic attack of metal -carbon
bonds, oxidative addition, and reductive elimination. It also includcd a chaptcr on tnc
structure and bonding of Main Group organometallic compounds.
This volume is concerned with thc use of organometallic compounds to crcatc carbon-
carbon bonds. Chaptcrs commissioned on thc use ofalkali metal, alkaline earth metal and
Group 111 organometallic compounds as well as Zieglcr-Natta polymerization olzfin
methathesis, and thc use of metal-arene compounds in carbon-carbon bond
formation havc not yet been complctcd and will be included in thc ncxt volume. The
remaining volume in the series will covcr the use of organometallic compounds in the
synthesis of carbon-hydrogcn and other carbon-element bonds, as well as the
preparation and use of Main Group organometallic compounds in organic synthesis.
In classifying organometallic compounds we have uscd Cotton’s hapto nomenclature
(9-) to indicate the number of carbon atoms directly linked to a single metal atom.
In common with other volumes in The Cliemistry of the Functional Groups scrics, the
emphasis is laid on the functional group treated and on thc effects which it exerts on the
chcmical and physical propcrtics, primarily in the imnediatc vicinity of the group in
qucstion, and secondarily on thc bchaviour of the whole molecule. The coveragc is
restricted in that material includcd in casily and generally available sccondary or tertiary
sources, such as Chemical Reviews and various ‘Advances’ and ‘Progrcss’ series as well as
textbooks (i.e. in books which arc usually found in the chemical libraries of universities
and research institutes) is not, as a rule, repeatcd in detail, unless i: is ncccssary for the
balanced trcatment of the subject. Therefore, cach of the authors has been asked not to
give an encyclopaedic coverage of his subject, but to concentrate on the most important
recent devclopments and mainly on material that has not been adequatcly covered by
reviews or othcr secondary sources by the time of writing of the chaptcr, and to addrcss
himself to a reader who is assumed to be at a fairly advanced postgraduate Icvcl. With
thcsc restrictions, it is realised that no plan can be devised for a volumc that would give a
VII
...
v111 Foreword
complete coverage of the subject with no overlap between the chapters, while at the same
time preserving the readability of the text. The Editors set themselves 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. Such a plan necessarily means that the
breadth, depth and thought-provoking nature of each chapter will differ with the views
and inclinations of the author.
The publication of the Functional Group Series would never have started without the
support of many people. Foremost among these is the late Dr Arnold Weissberger, whose
reassurance and trust encouraged the start of :he task. This volume would never have
reached fruition without and Mrs Baylis’s and Mrs Hunt’s help with typing and the
efficient and patient cooperation of several staff members of the Publisher, whose code of
ethics does not allow us to thank them by name. Many of our colleagues in England, Israel
and elsewhere gave help in solving many problems, especially Professor Z. Rappoport.
Finally, that the project ever reached completion is due to the essential support and
partnership of our wives and families.
Shrivenham, England FRANK HARTLEY
Jerusalem, Israel SAUL PATAI
contents
1. Carbon-carbon bond formation using tin and lead organometallics 1
V. G. Kumar Das and C.-K. Chu
2. Carbon-carbon bond formation using organometallic compounds of zinc,
cadmium, and mercury 99
L. Miginiac
3. Carbon-carbon bond formation using q3-allyl complexes 143
Part 1. q3-Allylnickel complexes 143
G.P. Chiusoli and G. Salerno
Part 2. g3-Allylpalladium complexes 163
J. Tsuji
Part 3. Other ,13-allyl transition metal complexes 200
F. Sato
4. Olefin oligomerization 205
0.-T. Onsager and J. E. Johansen
5. Alkyne oligomerization 259
M. J. Winter
6. Transition metal carbonyls in organic synthesis 295
J. A. Davies and R. J. Shaver
7. Olefin and alcohol carbonylation 335
G. K. Anderson and J. A. Davies
8. Olefin hydroformylation 361
J. A. Davies
9. The Fischer-Tropsch synthesis 391
G. Henrici-Olive and S. Olivi
10. Olefin Carbonylation 435
D. M. Fcnton and E. L. Moorehead
Author index 447
Subject index 479
ix
List of Abbrewiatiows Used
In order to economize on printing expenses, whenever possible abbreviations are used
instead of full names of radicals and instead of explicitly drawn structures. The following
list, arranged alphabetically, contains most of these abbreviations.
A appearance potential
Ac acetyl (CH,CO)
acac acetylacetone
ac acrylonitrile
acacen
bis(acety1acetonate)ethylenediamine
Ad adamantyl
aibn azobisisobutyronitrile
all ally1
An actinide mctal
aP antiplanar
aPPe P h AsCH CI-I P P h
Ar aryl
bae
bis(acety1acetonate)ethylenediamine
biPY 2,2'-bipyridyl
benzyl
BZ
Bu butyl (also t-Bu or Bu')
cd circular dichroism
cdt (E,E,E)-cyclododeca- 1,5,9-triene
cht cycloheptatriene
CI chemical ionization
CIDNP chemically induced dynamic nuclear polarization
CNDO complete neglect of differential overlap
coct cyclooctene
1,5-cod cycloocta- 1,5-diene
cot cyclooctatetraene
CP q'-cyclopentadienyI
CP* q5-pentamethylcyclopentadienyl
C.P. cross-polarization
CY cyclo hexyl
dba dibenzylideneacetone
dbn l,S-diazabicyclc[ 5.4.0]non-5-ene
xi
xii List of abbreviations used
dbu
1,8-diazabicyclo[5.4.0]undec-7-ene
dccd dicylohexylcarbodiimide
def diethyl fumarate
diars o-bis(dimethy1arsino)benzene
dibah diisobutylaluminium hydride
diop
2,3-o-isopropylidene-2,3-dihydroxy1-, 4-bis(diphenylphosphino)butane
dme 1,2-dimeth oxyethane
dmfm dimethyl fumarate
dmm dimethyl maleate
dmpe bis(
1,2-dimethylphosphino)ethane
dotnH
bis(diacetylmonoxime)propylene-l,3-diamine
dPm dipivaloylmethanato
dPPb bis( 1,4-diphenylphosphino)butane
dPPe bis( 1,2-diphenylphosphino)ethane
dPPm bis( 1,l -diphenylphosphino)methane
dPPP bis( 1,3-diphenylphosphino)propane
dmso dimethyl sulphoxlde
El,, half-wave potential
ece electron transfer-chemicai step-further electron transfer
ee enantiomeric excess
EI electron impact
peak potential
EEPS CA electron spectroscopy for chemical analysis
Et ethyl
eV electronvolt
Fc ferrocene
FD field desorption
FI field ionization
fmn fumaroni trile
fod F,C(CF,),COCH =C(O)C( CH,),
s)(co)z
FP F~(W,H
FP* Fe($-C,H,)(CO)(PPh,)
FT Fourier transform
Fu fury1 (OC,H ,)
Hex hexyl (C,H I,)
h fac hcxafluoroacetone
hfacac hexafluoroacetylacetonato
hmdb hexamethyl(Dcwar)benzene
hmpa hexamethylphosphoramide
hmpt hexamet hylphosphorotriamide
HOMO highest occupied molecular orbital
I ionization potential
ICR ion cyclotron resonance
ionization potential
1,
INDOR inter-nuclear double resonancc
LCAO linear combination of atomic orbitals
...
List of abbreviations used
Xlll
Ida lithium diisopropylamide
Ln lanthanide metal
LUMO lowest unoccupied molecular orbitals
M metal
A4 parent molecule
ma paleic anhydride
MAS magic angle spinning
tn-cpba nt-chloroperbenzoic acid
Me methyl
MNDO modified neglect of diatomic overlap
mnp 2-methyl-2-nitrosopropane
Naph naphthyl
nbd norbornadiene
nbs N-bromosuccinimide
nmP N-methylpyriolidone
OA o-allylphenyldimethylarsine
Pe pentenyl
Pen PentYl (C5H I I-)
phen o-phenanthrolinc
Pip piperidyl (C,HIoN-)
Ph phenyl
pmdeta
pentamethyldiethylenetriamine
PPm parts per million
Pr propyl (also i-Pr or Pr')
PRDDO partial retention of diatomic differential overlap
PYr PYridYl (C5H4N)
pyrazol yl
PZ
Quin quinolyl (NC,H,)
R any radical
RT room temperature
salen bis(salicy1aldehyde)et hylenediamine
salophen bis(salicyla1dehy de)-o-phen ylenediaminc
sce standard calomel electrode
set single electron transfer
SOMO singly occupied molecular orbital
synplanar
SP
SPT selective population transfer
t ba t ri benzylideneacet ylacetone
tcne tetracyanoet hylene
thf tetrahydrofuran
Thi thicnyl (SC,H,)
tmed tetramethylethylenediamine
tms tetramethylsilane (only used in this context as a frec standing symbol)
tms trimethylsilyl (only used in this context either with a dash after it or adjacent
to a chemical symbol)