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Book Review Comprehensive Handbook on Hydrosilylation. Edited by B. Marciniec

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BOOKS
densation reactions of alcohols and thiols.
coupling reactions of aromatic compounds, and aldol condensations. Chapter 13 deals with the thermal and hydrolytic decomposition of a wide variety
of pesticides, which is very important
from the viewpoint of protection of the
environment; examples of the degradation of pesticides and decomposition of
organic peroxides are discussed. Chapter 14 summarizes reactions of carbonyl
compounds. the C O group being probably the most versatile functional group in
organic chemistry. The reactions described include the formation of acetals
and ketals, condensation reactions with
amines and anilines. Knoevenagel condensations, and carbonyl group deprotection. Reactions of carboxylic acids and
derivatives with alcohols, arenes, and
ethylene are described in Chapter 15.
Chapter 16 describes synthesis of amino
acids, polymerization of amino acids, reactions of nucleotides, and formation of
peptides from amino acid adenylates.
Lastly. Chapter 17 contains the miscellaneous reactions which are not discussed in
the previous chapters. The book ends with
a glossary and subject index.
Balogh and Laszlo have produced a
book that sets new standards. They inform the readers expertly, comprehensively, and without unnecessarily lengthy detail about the capabilities and range of
applications of the various clay catalysts
described. The book is nicely written and
each chapter contains a separate list of
references. It can be recommended unreservedly for the chemist working in
academia or industry who wants detailed
information about the applications of clay
catalysts in organic synthesis.
Zeolite, Clay and Heteropoly Acid
in Organic Reactions. By Y; Zzumi,
K. UrahP and M . Onaka. VCH Verlagsgesellschaft,
Weinheim/VCH
Publishers, New York, 1992.
166 pp., hardcover DM 128.00.ISBN 3-527-2901 1-7/1-56081-700-3
This book by Y. Izumi, K. Urabe and
M. Onaka describes the applications of
solid catalysts in organic reactions. It contains three chapters with 350 references,
giving a detailed survey of the state of research on this topic up to the end o f 1991.
The first chapter comprises three sections giving a brief introduction to organic
reactions on zeolites and montmorillonite
clay. Each section (except the introduction) is divided into subsections discussing
different reactions. The topics covered are
the use of acid and base sites of zeolites in
Aii,qcw. C ’ l w i i .
Iiir
Ed. Eiigl. 1994. 33. h’o. I N
the 0-alkylation of alcohols to ethers, Nmonoalkylation of aniline derivatives, ring
opening of epoxides, regioselective bromination with adsorbed bromine on zeolite,
aldol reactions, Michael addition reactions, addition of ester enolates to ynoates,
and carbon-carbon bond forming reactions.
Chapter 2 is devoted to clays which are
potential catalysts in organic synthesis.
After a short introduction to clays, this
chapter discusses the structure and composition o f clays, factors determining
their catalytic efficiency, and new catalytic aspects of synthetic clays. Other topics
covered are the selective hydroisomerization of n-hexane, selective dehydrogenation of cyclohexane, selective etherification of n-butyl alcohol, selective hydrolysis of chlorobenzene to phenol, and
metathesis reaction of propene.
Chapter 3 discusses the usefulness of
heteropoly acids in organic synthesis. This
chapter describes the fundamental chemistry of heteropoly acids, and their uses in
acid-base and redox molecular catalysis
for various types of organic reactions.
The authors have succeeded in providing the reader with a lot of information
regarding organic reactions over solid catalysts. The summary tables, reaction
schemes, and literature references make it
easier for the reader to get more deeply
involved in this wide-ranging field of research and facilitate quick access to the
original papers.
The book is a useful addition to the literature on zeolite, clay, and heteropoly
acid in organic reactions. To those who
are seriously interested in organic reactions using solid catalysts, I can recommend reading this neat and well written
book.
Ganesh Pandey
Organic Chemistry (Synthesis) Division
National Chemical Laboratory
Pune (India)
Comprehensive Handbook on Hydrosilylation. Edited by B . Marciniec.
Pergamon, Oxford, 1992. 754 pp.,
hardcover
E 150.00.-1SBN 0-08040272-0
This book edited by Bogdan Marciniec
is an extension of the Polish version of
Hydrosil.vlation, published in 1981. The
present monograph aims to provide a
complete coverage of the literature from
1965 up to the beginning o f 1990. Over
1360 literature references and 750 patents
are included. The volume is divided into
two parts. The first part is a critical survey
C VCH Verlug.sgesrll.sr.huflmhH. 0.69451 Weinheim,1994
of the scope and application of hydrosilylation reactions. The second part is a truly
extensive tabulation of published hydrosilylation reactions from 1965 to 1990.
Part I consists of six chapters which
deal with the systematic trends of the hydrosilylation reaction, focusing on catalyst, silane, and unsaturated substrate.
Chapter 1 is a very brief introduction discussing the rationale and organization of
the subject matter and its relation to other
reviews in the field. Chapter 2 is a survey
o f mechanistic aspects of the hydrosilylation reaction including free radical, acid
and base catalysis, and transition metal
catalyzed reactions. Chapter 3 deals with
the reactivity of the major classes of unsaturated organic compounds and their
utility in the synthesis of organosilicon
compounds. This chapter is organized by
compound class with separate discussions
of alkenes, dienes. alkynes, carbonyls, and
other functional groups. The effects o f
substituents on the organosilane reagents
with regard to reaction rate and regio- and
stereoselectivity are described in Chapter 4. The chapter also includes practical
applications to the synthesis of organosilicon monomers. Chapter 5 is a short discussion of the hydrosilylation reactions of
unsaturated organosilicon compounds,
which are important both as models for
activated curing processes and as routes
to the synthesis of carbosilane oligomers
and polymers. Finally, Chapter 6 covers
some practical applications o f the hydrosilylation reaction including the role of
organosilanes as coupling agents and as
reducing agents for organic substrates.
The use of hydrosilylation in polymer
modification is also discussed. The topics
covered in Part I are very generously illustrated by examples, but sometimes these
get in the way o f the guiding principles.
Also numerous typographical errors,
nomenclature lapses, and hard-to-read
figures make this section of the book difficult for browsing or casual reading.
Part IT of this volume is a nearly exhaustive compilation of hydrosilylation
reactions from 1965 to 1990, and includes
both literature and patent references. The
425pages of data are organized into
tables which list initial reagents, reaction
conditions (catalyst, temperature, time,
solvent, etc.), products with yields, and
references. The primary division of the
tables is according to trisubstituted silanes
of increasing complexity (Si, C, and H
numbers), followed by the type and complexity of unsaturated organic substrates
(C and H numbers). The table is keyed to
a separate bibliography giving the appropriate literature references. Patents are
identified not only by the patent number
BOOKS
but also by an abstract number in Cheniical Abstracts or Ref: Zh. Khim. Also included in this part of the volume is a key
to abbreviations for solvents and functional groups and a glossary containing
structural diagrams for some of the more
complex organic substrates and products.
Perhaps one of the greatest weaknesses of
this type of tabular presentation is the
constant need to move back and forth between the main table and the supporting
glossaries. This is particularly relevant
since many of the abbreviations are nonstandard (for example, c stands for chloroform), and for complex structures it is
necessary to constantly refer to a glossary
for structures which are identified only by
numbers in the main table. However, this
tabulation is a commendable feat and
many will find this section of the book by
far the most useful.
The treatment of hydrosilylation in the
first six chapters is largely by detailed examples, and consequently it would not be
a good introduction for the novice and
should not be used as a textbook. However. the wealth of information which is
presented in this volume should be of
tremendous value to the practitioner of
the hydrosilylation reaction. whether it be
in an industrial or academic setting. As
such, this book is an indispensable reference source.
Mark Fink
Department of Chemistry
Tulane University
New Orleans, LA (USA)
Iron- Carbene Complexes. (Series:
Scripts in Inorganic and Organometallic Chemistry, Vol. 1.) Edited
by W Petz. Springer, Heidelberg,
1993. 202pp., paperback DM 68.00.
-ISBN 3-540-56258-3
The celebrations were premature! Anyone who hoped that this new series from
the Gmelin-Institut fur Anorganische
Chemie would make it possible to build
up a “home Gmelin” at a realistic and
affordable cost will be bitterly disappointed. The initial concept, which is again
stated in the preface to the first volume of
this series. sounds very good: “...the new
Gmelin series will review selected areas of
inorganic and organometallic chemistry
in textbook style. It will provide the lecturer, the advanced student. and the research chemist with a digest of the main
features of each topic.” As the first topic
the publishers have chosen iron-carbene
and iron-vinylidene complexes in which
the iron atom also has a q5ligand (C,H,
or one of its derivatives). This is a sensible
restriction when one considers that the
systematic preparation and study of
Fischer carbene complexes has now been
going on for nearly thirty years. and it is
no longer realistic to expect the whole of
this extensive subject, with all the possibilities of central metal atom and substitution pattern. to be covered in a single
monograph. The area treated here corresponds exactly to the volume of the original Gmelin-ffundbuclz der Anorgunischen
und Mriallor~unisclien Cheniie with the
title “Organoiron Compounds B16a”,
containing about 260 pages.
To anyone familiar with the density of
data in Gmelin. the task of producing a
“digest of the main features” of this subject must seem rather like trying to write a
short summary of the national postcode
index. Practically all the shortening needed to compress the subject into 200 pages
for the new publication Iron-Carhenr
Complexes has been achieved by taking
out the formula index completely and
eliminating all the literature references
and the journal citations from the text of
the original Gmelin (although, curiously,
on the bottom line of p. 168 the last of the
references has survived the massacre of its
brothers).
However, this has severely reduced the
book’s potential readership. Specialists
working on iron or other carbene complexes, after a first nibble at a topic, need
to be given direct access to the original
publications. One can perhaps envisage
the book being used as a quick reference
source for spectroscopic and X-ray structural data, but this use is greatly hindered
by the incompleteness of the numerical
data and the lack of a detailed overall index. Lecturers and students seeking a general overview of carbene complexes (or
even one confined to iron as the central
metal atom) will quickly abandon this
book, since despite the declared aim of
producing a work in “textbook style”, this
is clearly not that but a collection of data.
The few general comments included at the
beginnings of individual chapters are either too superficial or so brief that they
cannot be understood without relevant
previous knowledge.
In this connection one must also mention the many printing errors. In many
cases parentheses are either missing or too
many in number, and more seriously there
are numerous spelling mistakes and incorrect formulas, sometimes altering the
meaning. Examples are “RHC=CNCH,”
instead of RHC=NCH, (p. 32) and ‘ T p (CO)(2D)FeC=CH” instead of Cp(C0)(2D)FeC=CH (p. 5 9 , and on page 122 a
rotational barrier is given as 7712 kJ/mol
instead of 77 2 kJ/mol. The “one-protein resonances” referred to on page 104
are presumably one-proton resonances.
There are also many errors in the figures.
In Figures XI1 and XITI (p. 54) the cyclopentadienyl ligand is shown as “H,C,” instead of H,C,, and the Fp-containing sidechain of compound XXVIII on page98
has an extra carbon atom. Although errors
such as these only cause a shake of the
head, the incorrect caption “(S,S)-chiraphos” under Figure IV (p. 184), which actually shows the R,R isomer, is inexcusable. Other errors that need no further
comment are the description of the diastereomeric complexes VII and VIII (p, 27)
as “enantiomeric cations”, and the labeling of the abscissa in the figure on page 55
as “Wavenumber in nm”.
Another source of annoyance is the lack
of a glossary explaining the abbreviations
used in the book, as also are the repeated
explanations of familiar compound name
abbreviations (e.g., dppe on pages 7, 10,
47, 178. 181, and 182). and the use of the
same abbreviation for different groups
(e.g., Fp* is used to represent (C,Me,)(CO),Fe on pp. 104, 124, and 125.
(C,H,Me)(CO),Fe on pp. 117 and 123,
and (C,H,)(CO),Fe on pp. 123 and 124).
The cross-references too show little sign of
having been carefully checked. As well as
references to the wrong chapters (pp. 114,
126, 158, 167), there are others mentioning chapters that do not even exist
(pp. 152, 1 58, 197) and methods of preparation that are not given (“Method IV”
on pp. 118, 121). These and many other
errors are quite unacceptable, especially
in a book of only 202 pages.
The verdict after looking through IronCarhene Complexes, which is also to be
regarded as an initial sample for the new
series Scripts in Inorganic and Organometallic Chemistry. is clear. By carrying out
some intensive work on correcting the errors, providing a formula index for
the whole work, and including all the references to original publications, the authors and the publishers would be performing a valuable service. not least to
themselves.
Gerhurd Roth
Fakultat fur Chemie
der Universitit Konstanz (FRG)
.25/O
Angrw. Cliem. Inl. Ed. E q I . 1994. 33, No. 18
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