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Book Review Chemistry of the Iron Group Metallocenes Ferrocene Ruthenocene Osmocene. Part I. By M

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ganic chemists who, without much previous knowledge, wish
to learn from the beginning about conformational analysis.
Two of the eight chapters are devoted to a short general
introduction to stereochemistry, four treat in detail the
conformations of alicyclic and one each the conformations
of heterocyclic and aliphatic compounds.
The numerous references (some even up to 1964) will help
those who wish to form their own opinion about this field,
which is of the utmost importance in many areas of organic
V. Prelog
[NB 489 a IE]
good idea to try an essentially non-mathematical treatment
it does not seem possible to follow this idea to the end.
Reference to “reducible” and “irreducible representation” is
avoided as long as possible; therefore arguments in which
these terms are nevertheless needed are not very convincing.
A reader who is not interested in mathematics and in understanding symmetry thoroughly, but who rather wants to get
an idea of how group theory can be used in practice, will
probably appreciate this book more than others on the same
W .Kutzelnigg
W B 491 IE]
Fundamentals of Carhanion Chemistry. By D . J . Cram. Organic Chemistry - A Series of Monographs. Edited by
A . T. Blomquist. Vol. 4. Academic Press. New York-London 1965. 1st edit., viii + 289 pp., numerous figs. and
tables, bound, $9.50.
In spite of the apparent antipodal relation between carbanions and carbonium ions, carbanion chemistry is much less
well defined and is much younger than carbonium ion chemistry as a field of work in its own right within organic chemistry. To carbanion chemistry belong molecules whose negative charge lies mainly or wholly on carbon. It includes therefore above all the chemistry of organic derivatives of the alkali metals, and extension of the acid-base concept to other
carbon acids than the classical “active methylene compounds”. Since there is n o comprehensive treatment of this
heterogeneous, rapidly developing field, one is eager to turn
to Cram’s book.
The critical survey of the thermodynamic and kinetic acidity
of carbon acids given in the first section is so good that it
alone would justify purchase of this book. A discussion of the
structure and stability of carbanions is followed by three
chapters on the stereochemistry of carbanions and electrophilic substitution reactions, which make up half of the book.
Their center of interest is the author’s own fundamental
work in this field. The conclusion is a racify written, brief
summary of molecular rearrangements that proceed by way
of carbanions.
Perusal of this monograph is strongly recommended t o all
who are interested in reaction mechanism. The author’s repute is guarantee f o r a competent and clear treatment of the
material. However, the book has some regrettable gaps. Important papers o n the stereochemistry of simple carbanions
are omitted and there is no mention of, for instance, the
class of high acidic hydrocarbons or ofradical ions. Work o n
organic compounds of the alkali metals, which is of such
supreme importance to carbanion chemistry, is mentioned
only in passing, showing the almost complete failure to
evaluate, in particular, the German literature, and without
that a standard textbook of carbanion chemistry would be
unthinkable. This does not diminish the value of Cram’s
book; it is indeed questionable whether a comprehensive
text o n the whole topic can yet (or still) be written. The reader
lays down the book with the wish that an equally good one
on other aspects of carbanion chemistry were available.
[NB 489 b IE]
G. Kobrich
Quantum Mechanics in Chemistry. By M. W. Hanna. W . A.
Benjamin, Inc., New York-Amsterdam 1965. 1st Edit.,
253 pp.. numerous figs. and tables, paperback $4.35,
bound $7.70.
Symmetry in Chemistry. By H. H. Jaffe‘and M. Orchin. John
Wilev & Sons. Inc., New York-London-Sydney 1965. 1st‘
edit., x + 191 pp., several figs. and tables, bound, E2.2.-,
paperback E1.lO.- (about $6.- and $4.20).
A few years ago there was a dearth of textbooks on group
theory that presented this field in a way suitable for chemists
or molecular physicists, but today there is a large choice of
such books. Joffe‘ and Orchin’s monograph is distinguished by
the simplicity of the presentation
After a lightly philosophical introduction on “Symmetry and
Beauty” the authors introduce the terms symmetry operations, multiplication of symmetry operations, symmetry
groups, and symmetry species clearly and convincingly with
the aid of examples familiar to chemists. Although it is a
This book is intended for undergraduates.
Mathematical methods and concepts that go beyond school
mathematics but are essential for an understanding of
modern theoretical chemistry are presented clearly and intelligibly in an introductory chapter. The fundamentals of
quantum theory are introduced axiomatically. It is didactically wise to treat rotations and vibrations of molecules as
the first applications of quantum mechanics, and only
thereafter the electronic structure of atoms and the theory
of the chemical bond. Therefore the book can be recommended also - and in fact particularly - as an introduction
to molecular spectroscopy.
The author is concerned mainly with defining the fundamental concepts precisely and in an understandable way. The
mathematical formulations are compact and conform to
international usage. The readen is not embarassed with
lengthy derivations. The well chosen problems allow him to
find the easier proofs himself, whereas for more complicated
ones he finds references to more detailed monographs. Each
chapter has a summary.
One should not expect from a textbook mtended for beginners
a survey of quantum chemistry. In fact it offers the minimum
of what a modern chemist shouId know about quantum
mechamcs. It is recommended particularly for those young
students who d o not mind some mathematics and are ready,
not just to read a textbook, but to study it carefully.
The printing is agreeable and clearly arranged. The only
error the reviewer found is the value of 1.37 A instead of
1.06 A for the equilibrium distance in H:.
W. Kutzelnigg
[NB 492 IE]
Chemistry of the Iron Group Metallocenes: Ferrocene, Ruthenocene, Osmocene. Part I. By M. Rosenblum. Interscience Publishers, New York,London-Sydney 1965. 1st
Edit., xv + 241 pp., numerous figs., bound, f4.15.-.
The development of the chemistry of organometallic compounds during the last ten years justifies the metaphor “explosive”. Consequently an attempt at a new edition of a book
such as E. Krause and A . von Grosse’s “Die Chemie der metallorganischen Verbindungen”, which contained all the metallorganic compounds known in 1937, would appear utopian. Interscience Publishers have now begun t o cover the
most important sections of organometallic chemistry by a
series of monographs edited by D . Seyferth. The first of
these is devoted to the metallocenes of the iron group,
with particular emphasis on ferrocene as the prototype of dicyclopentadienylmetal compounds.
The first three chapters of present volume deal with the
preparation, electronic structure, bonding, and physical
properties of metallocenes. The bonding, which has in the
past been the subject of controversial discussion, is purposely
not treated in full detail; only the important results based on
MO treatment are presented. Chapters 4, 5 , and 6 deal with
the acyl-, alkyl-, and aryl-metallocenes that were obtained by
replacement of ring protons, their preparation illustrating
Angew. Chem. internat. Edit.
Vol. 5 (1966) 1 No. 8
also the reactivity of the starting materials M(CsH5)z (M = Fe,
Ru, or 0 s ) . The mechanisms of the replacement reactions are
discussed in detail, whereby attention is directed to the
problem of the “aromatic character of metallocenes”. At the
end of each of these chapters all the known derivatives and
their most important properties are tabulated.
The author has contributed to the development of this field
from its very beginnings. He has managed to extract what is
most worthwhile from more than 1000 papers and he has
given fair consideration to the contributions of the various
schools. The literature is almost completely covered up to the
middle of 1963, and many results are included that had not
then been published. The outward appearance of the book is
very pleasing but it is unfortunate that some misprints have
escaped correction.
The reviewer hopes that the second Part will turn out as well
as the present Part I, so that there will then be a standard
work on the chemistry of the metallocenes of the iron group.
H. Werner
[NB 486 IE]
The Chemistry of the Vitamins. By S. F. Dyke. J. Wiley &
Sons Ltd., London-New York-Sydney 1965. 1st Edit.,
363 pp., several figs., bound, E3.7.-.
This book is the sixth in the series “The Chemistry of Natural
Products” edited by K . W . Bentley. It treats the well-known
vitamins or vitamin groups, and in particular the elucidation
of their structures and their synthesis. It describes also relations between structure and activity of the vitamins, and their
biosynthesis and biological function, but not their isolation
which is often so troublesome and in which the natural products chemist would probably be interested. The material is
arranged in a useful and clear manner; understanding is
facilitated by the numerous formulae and figures. At a first,
superficial examination one is glad to have found a short
introduction that may be useful for lectures and for student
use. Closer scrutiny shows, however, that the book is not intended as a n introduction or a textbook. It contains mainly
references to original papers, including some from the previous century, and it is not clear to the readeron what basis they
were chosen. Wherever the chemistry (determination of
structure and synthesis) of the vitamins is complete, citation
of a n appropriate review would have sufficed. On the other
hand there are veryfew references to papers later than 1960:
the reader is given the impression that the chemistry of the
vitamins came to a standstill in that year. N o indication is
given of the aims of present-day vitamin chemistry or of the
properties and reactivity of vitamins in the molecular-biological sense. So one is left in the dark as to the audience for
which the book is intended. Further, the subject matter overlaps extensively with that of “Vitamins and Coenzymes” by
A. F. Wagner and K . Folkers which was published a year
K . Bernhauer [NB 485 IE]
ing point, and molecular weight follow. For each substance
the spezific rotation, conditions of measurement (wavelength,
temperature, concentration, and solvent) are then given, with
references. The list of references is very clearly arranged according to year and journal at the end of the Tables. An
author index and a n alphabetic index of substances, including
all the trivial names, close this comprehensive volume. Skilful
arrangement of the tables and indexes make it a simple matter
to find any required compound in spite of the new systematic
and often unfamiliar names used.
The specific rotations are generally given as averages of the
published data, together with their range of variation. In this
respect the literature is considered critically and the less certain values are designated as such. Revised formulae are included up to 1963 inclusive, and occasionally the authors
themselves suggest new structures on the basis of the specific
rotations. This, of course, admits the danger of correct formulae being changed, e.g. because of an erroneous measurement or a misprint in the original paper. Restriction of space
prevented curves or table of optical rotatory dispersion from
being reproduced, but when such measurements exist the appropriate paper is cited. Such citations are often as “personal
communications”; presumably, however, these data have
meanwhile all been published.
A comprehensive set of tables such as this is of value only if
truly complete and essentially free from error. As a test the
reviewer undertook a large number (about 50) of random
tests. As luck hat it, in the first\cabe a page number was wrong,
in the second a reference was missing and in the third a n inbut a11 the others were correct.
correct reference was given
One cannot but admire the authors’ achievement in not
merely providing a complete collection of the published [a]
values for the steroid field but also, as a by-product as it were,
a n excellent review of the literature for most of the steroids recorded to date. Since the specific rotation is often a better criterion than the melting point it is cited by almost all authors.
Instead of searching several Collective Indexes of Chemisches
Zentralblatt or Chemical Abstracts for a particular compound one can use these tables to cover at least 95 % of the
literature up to 1960. In this connection it is particularly valuable that the derivatives are listed immediately after the
parent compound in the alphabetical index.
The “Pouvoir Rotatoirt Natural” is thus of the greatest value
to steroid chemists, not merely because of the specific rotations collected therein, but also especially as a source of
references. This fact justifies the very high price; though this
price will certainly prevent very wide distribution, each group
of steroid chemists, at least, should possess a copy of this
standard work; the saving in time as a source of references
will soon have reimbursed the cost.
G . Snatzke
[NB 484 IE]
Condensation Polymers: By Interfacial and Solution Methods.
By P . W . Morgan. John Wiley & Sons, New York-London561 pp., numerous figs.,
Sydney 1965. 1st Edit., xviii
several tables, bound, E9.10.-.
Constantes S6lectionnees Pouvoir Rotatoire Nature1 (Selected Values of Optical Rotatory Power). By J . Jacques,
H. Kagan, G . Ourisson, and S . Allard. Tables de Constantes
et DonnCes Numeriques. No. 14. I a . Steroldes. Pergamon
Press, Oxford-Paris 1965. 1st Edit., 1031 pp., about $54.
In 1956 there appeared the first collection of specific rotations
of about 8000 steroids included in the literature up to 1952.
In the present volume the literature is covered up to 1960 inclusive, and data are given for more than 21000 steroids.
This, incidentally, provides an impressive picture of the
growth of the literature in this field.
The introduction, in French and English, describes in readily
intelligible form the arrangement adopted and the nomenclature. The recommendations of the IUPAC Nomenclature
Commission for Steroids have been followed strictly, with
extensions, where necessary, in the same spirit. In the main
part of tne work the compounds are arranged according to
molecular formula, and the systematic name (French), meltAngew. Chem. internat. Edit. I Vol. 5 (1966) No. 8
Paul W . Morgan’s book is the tenth volume of a series on
polymers edited by H . F. Mark and E. H . Immergut. Its aim
is to present an up-to-date review of polymer chemistry.
The author has limited his treatment to condensation polymerization and has collected his material under several main
headings. First he treats polycondensation methods which
below 100 “C generally lead to linear polymers and in which
the components react at a n interface. The preparation of polyamides, polyureas, polyurethanes, polysulfonamides, polyphosphonamides, and polyesters is described in detail.
The preparative procedures are accompanied by very clear
descriptions of the unusual properties of the products obtained by interfacial-polymerization and these are compared,
where appropriate, with polymers obtained in the classical
way. Noteworthy is the large number of monomers that the
author describes as suitable for low-temperature condensation.
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chemistry, part, book, group, metallocene, osmocene, iron, ruthenocene, review, ferrocenyl
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