Organometallic Compounds of Iron

485 Pages·1985·26.487 MB·English

by  G. R. Knox (auth.), G. R. Knox (eds.)

Organometallic Compounds of
Iron
Organometallic Compounds of
Iron
Edited by
G. R. Knox
University of Strathclyde
SPRINGER-SCIENCE+BUSINESS MEDIA, B.V.
ISBN 978-0-412-26820-5
© 1985 Springer Science+Business Media Dordrecht
Originally published by Chapman and Hali Ltd in 1985
AII rights reserved. No part of this book may be reprinted, or reproduced or
utilized in any form by any electronic, mechanical or other means, now known or
hereafter invented, including photocopying and recording, or in any information
storage or retrieval system, without permission in writing from
Springer-Science+Business Media, B.V.
ISBN 978-0-412-26820-5 ISBN 978-1-4899-7168-5 (eBook)
DOI 10.1007/978-1-4899-7168-5
Library of Congress Cataloging in
Publication Data
Main entry under ti tie:
Organometallic compounds of iron.
Includes index. British Library Cataloguing in
1. Organoiron compounds-Handbooks, Publication Data
manuals, etc.
Organometallic compounds of iron.
1. Knox, G. R., 1934-
QD412.F4'74 1985 547' .05621 84-29355
1. Organoiron compounds
1. Knox, G.R.
547'.05621 QD412.F4
Contents
Preface pagevn
Introduction
IX
Fe Iron 1
Name Index 351
Molecular Formula Index 395
CAS Registry Number Index 447
v
This Sourcebook has been reproduced in part from the
Dictionary of Organometallic Compounds. If you find it
useful and you would like full coverage, then why not buy
the Main Work for your library
DICTIONARY OF
ORGANOMETALLIC
COMPOUNDS
The recent growth in organometallic chemi try
has led to an explosion in the
number of organometallic compounds
discovered or synthesized.
How can scientist working in this
area locate reliable data on all
really important organometallics?
The answer lje in the new Dictionary
of Organometallic Compound ,
published in November 1984.
• provides within 15,000 Entrie an exten ive • provides a continually up-to-date information
yet selective compilation of the mo t important system with Annual Supplements
organometallic compounds • entrie compiled by subject expert under
• for each compound, detail of tructure, upervi ion of a prestigiou international
physical and chemical properties, reaction and advisory board
references are provided in clearly set out and • a time- aving, co t- aving and reliable
easily scanned Entries re ource essential to all u ers of organometaUic
• offers access to compounds by structure, compounds
molecular formula, chemical name, or CAS
Registry Number From a review by F.A. Cotton, Texas A & M
University
• the structure index contains reduced images
of all the structure diagrams in the ection - a 'This extraordinarily useful compendium is
unique feature which allows users to 'brow e', one that no chemical enterprise having the
and to appreciate quickly the full range of types slightest involvement in organometallic
of compounds which have been synthe ized chemistry would want to be (or would be
wise to be) without.'
Publication date: November 1984 ISBN: 0 412 247100
286 x 213mm 3 000 page in three volume
For further information please write to The Promotion Department,
Chapman and Hall, 11 ew Fetter Lane, London EC4P 4EE.
s
CHAPMAN AND HALL
11 New Fetter Lane, London EC4P 4EE
733 Third Avenue, New York NY 10017
Preface
This is one of the first volumes to be published in the series of Chapman and Hall
Chemistry Sourcebooks which provides carefully tailored information to workers in
specialized areas of chemistry. The information contained in this book is derived from the
Dictionary of Organometallic Compounds, published in November 1984.
Organoiron compounds are amongst the most widely studied group of organometallics.
Since the discovery of ferrocene in 1951 there has been a huge growth in the number of
organoiron derivatives. Interest is now turning to the use of these compounds in organic
synthesis, since the binding of an iron atom to an organic ligand changes the way in which
reagents act on the ligand and thus gives rise to a new range of possible synthetic pathways.
The large variety of organoiron compounds and their reactions will ensure that this
particular compendium will reach a wide audience.
The databank on the properties of organometallic compounds, which is represented in
its current form by the Dictionary of Organometallic Compounds and its subset
publications such as this volume, will be kept continuously up-to-date. Supplements to the
main Dictionary will appear annually and revised editions of this Sourcebook will be
published from time to time as demands permits.
G.R.Knox
Vll
Introduction
1. Using the Sourcebook (2) Any compound with an established use, such as
in catalysis, as a synthetic reagent or starting material.
The entries in this Sourcebook are arranged in order
(3) Other compounds of particular chemical,
of molecular formula according to the Hill
structural, biological or historical interest, especially
convention (i.e. C, then H, then other elements in
those thought to exhibit unusual bonding characteris
alphabetical sequence of element symbol; where no
tics.
carbon is present, the elements including H are
ordered strictly alphabetically). Some compounds which are not considered
Every entry is numbered to assist ready location sufficiently important to justify separate entries of
and the entry number consists of the symbol Fe their own have been included as derivatives in the
followed by a five-digit number. entries of other compounds. These may include for
example:
Indexes
(1) Organic derivatives in the classical sense, e.g.
There are three printed indexes: a name index which
the various esters of ferrocenecarboxylic acids.
lists every compound name or synonym in alpha
(2) Donor-acceptor complexes.
betical order; a molecular formula index which lists
(3) The various salts of an anion or cation. In
all molecular formulae, including those of deriva
nearly every case, the entry for an ionic substance
tives, in Hill convention order; and a CAS registry
refers to the naked anion or cation, and the molecular
number index listing all CAS numbers included in the
formula, molecular weight and CAS registry number
Sourcebook in serial order. All indexes refer to the
given for the main entry are those of the ion, in
entry number. In the name index an entry number
agreement with current CAS practice. Salts of the ion
which follows immediately upon an index term means
with various counterions are then treated as
that the term itself is used as the entry name but an
derivatives and the molecular formulae of all of these
entry number which is preceded by the word 'see'
are given.
means that the term is a synonym to an entry name. In
( 4) Oligomeric compounds. Where a compound is
all three indexes an entry number which is preceded
known in several states of molecular aggregation
by the word 'in' refers the reader to a specified
these are all included in the one entry, which usually
stereoisomer or derivative which is to be found
refers to the monomer. Compounds which are known
embedded within the particular entry.
only in dimeric form are entered as such, but the
In addition to the three printed indexes, a graphical
hypothetical monomers are included as derivatives to
structure index precedes the section containing the
ensure that the names and molecular formulae of the
entries, allowing the rapid visual location of
monomeric forms occur in the indexes.
compounds of interest. The structure index repro
duces all structure diagrams in reduced size and All names and molecular formulae recorded for
printed in entry number order. derivatives occur in the Name and Molecular
The following paragraphs summarize important Formula Indexes respectively.
considerations in compiling the information in this
Sourcebook. For more detailed information, see the 3. Chemical Names and Synonyms
Introduction to the Dictionary of Organometallic
The naming of organometallic compounds is
Compounds from which this Sourcebook derives.
frequently problematic and so in selecting the range
of alternative names to present for each compound or
2. Compound Selection derivative, editorial policy has been to report names
which are found in the literature, including Chemical
In compiling this Sourcebook the aim has been to
Abstracts, and not to attempt to impose a system of
include from the primary literature up to mid 1983:
nomenclature. The editorial generation of new
(1) Compounds representative of all important names has therefore been kept to a minimum
structural types (typically, the parent member of each required by consistency. Most names given in the
series, where known, together with a selection of its Sourcebook are those given in the original paper(s)
homologues). and in Chemica/Abstracts.
ix
Introduction
Names corresponding to those used by CAS during review of the whole subject. In addition to sections
the 8th, 9th, and lOth collective index periods for each element there are chapters on the use of
(1967-71, 1972-6 and 1977-81 respectively) are organometallics in organic synthesis and catalysis.
labelled with the suffixes SCI, 9CI and lOCI Comprehensive Inorganic Chemistry, Trotman
respectively. Dickenson, A.F. et al. Eds, Pergamon, Oxford, 1973.
Contains information about organometallics as well
as discussions of oxidation states, coordination
4. Toxicity and Hazard Information
chemistry and analysis of the metals.
Toxicity and hazard information is highlighted by the Gmelins Handbuch der Anorganischen Chemie,
sign [> which also appears in the indexes. 8th Edn, Springer-Verlag, Berlin. Some volumes of
Gmelin covering organometallic compounds have
All organometallic compounds should be treated as if
been updated relatively recently and can therefore be
they have dangerous properties.
consulted for comprehensive data on some types of
The information contained in the Sourcebook has organometallics. Some Gmelin element sections,
been compiled from sources believed to be reliable. however, are many years out of date.
No warranty, guarantee or representation is made by Houben-Weyls Methoden der Organischen Che
the Publisher as to the correctness or sufficiency of mie, 4th Edn, Band XIII, Metallorganische Verbin
any information herein, and the Publisher assumes no dungen, Thieme-Verlag, Stuttgart.
responsibility in connection therewith. The Chemistry of the Carbon-Metal Bond, Hartley,
The specific information in this publication on the F.R. and Patai, S. Eds, Wiley, New York, 1982-.
hazardous and toxic properties of certain compounds Contains sections on the synthesis, analysis and
is intended to alert the reader to possible dangers thermochemistry of various classes of organometallic
associated with the use of those compounds. The compounds.
absence of such information should not, however, be Transition-Metal Complexes of Phosphorus,
taken as an indication of safety in use or misuse. Arsenic and Antimony Ligands, McAuliffe, C.A.
Ed., Macmillan, London, 1973.
Methods of Elemento-Organic Chemistry, Koches
5. Bibliographic References
hkov, K.A. Ed., North Holland, Amsterdam, 1967.
The selection of references is made with the aim of MTP International Review of Science: Inorganic
facilitating entry into the literature for the user who Chemistry, Series 2, Emeleus, H.J. Ed., Butter
wishes to locate more detailed information about a worths, London; University Park Press, Baltimore,
particular compound. Reference contents are fre 1974-5.
quently indicated using mnemonic suffixes. In Advances in Organometallic Chemistry, Academic
general recent references are preferred to older ones, Press, 1964-.
and the number of references quoted does not Annual Surveys of Organometallic Chemistry,
necessarily indicate the relative importance of a Elsevier, 1964-7.
compound. Organometallic Chemistry Reviews, Elsevier,
Journal abbreviations generally follow the practice 1966-7.
of Chemical Abstracts Service Source Index ( CASSI). Organometallic Chemistry Reviews, Section A:
In patent references, no distinction is made between Subject Reviews 1968-72.
patent applications and granted patents. Organometallic Chemistry Reviews, Section B:
Annual Surveys 1968-74.
Journal of Organometallic Chemistry: This incor
6. Sources of Further Information
porates reviews and surveys after the discontinuation
The following books and review series provide more of the two series of Organometallic Chemistry
information about various aspects of organometallic Reviews.
chemistry. Lists of reviews specific to organic Organometallic Chemistry. 1972-, (Specialist
compounds of iron may be found in the next section. Periodical Reports), RSC.
Coordination Chemistry Reviews, Elsevier, 1966-.
General Progress in Inorganic Chemistry, Interscience,
Comprehensive Organometallic Chemistry, Wilkin 1959-.
son, G. et al. Eds, Pergamon, Oxford, 1982. This Advances in Inorganic Chemistry and Radio
book represents the most complete and up to date chemistry, Academic Press, 1959-.
X
Introduction
Analysis Mann, B.E. Eds, Academic Press, London, 1978.
Scott's Standard Methods of Chemical Analysis, 13C NMR Data for Organometallic Compounds,
Furman, N.H. Ed., 6th Edn, Van Nostrand, New Mann, B.E. and Taylor, B.F. Eds, Academic Press,
York, 1962. London, 1981.
Crompton, T.R., Chemical Analysis of Organo Spectroscopic Properties of Inorganic and Organo
metallic Compounds, Academic Press, London, metallic Compounds, 1968-, (Specialist Periodical
1973. Reports), RSC.
Spectroscopy Handling
Nuclear Magnetic Resonance Spectroscopy of Nuclei Shriver, D.F., The Manipulation of Air-Sensitive
Other than the Proton, Axenrod, T. and Webb, G.A. Compounds, McGraw-Hill, 1969.
Eds, Wiley, London, 1974. Organometallic Syntheses, Academic Press, New
NMR and the Periodic Table, Harris, R.K. and York, 1965, Vol. 1.
xi