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Book Review The Chemistry of the Fullerenes. By A. Hirsch

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synthesis: the ferrocenylmethyl group of
the side-chain contains suitable functional
groups, the planar chirality of the 1.2-substituted ferrocene cannot racemize, both
mono- and diphosphines can be prepared
from the same chiral source. and lastly the
characteristic orange-red color of the ferrocene derivative facilitates chromatographic work-up. Part I ends with a
chapter on “Enantioselective Addition of
Dialkylzinc to Aldehydes Catalyzed by
Chiral Ferrocenyl Aminoalcohols” (Y.
Butsugan. S. Araki, and M. Watanabe).
Part 11 again begins with a report on chiral ferrocenes (Ch. 4, G . Wagner and R.
Herrmann). However, it was not clear to
me why this excellent contribution was
not included in Part I, where synthetic aspects had already become an important
part of the discussions.
In Chapter 5, “Ferrocene Compounds
Containing Heteroelements” (M. Herberhold). the inorganic chemist’s heart will
certainly beat a little faster on discovering
Ferrocenes. Homogeneous Catalysis. with pleasure that it contains all those
Organic Synthesis. Materials Science. compounds that would otherwise require
Edited by A . Togni a n d 7: Hayashi. laborious searching through the Gmelin
V C H Verlagsgesellschaft, Weinheim, volumes or recent original papers. It is es1995. 540 pp., hardcover DM 248.00, pecially commendable that this and several other chapters include some ”Notes
$ 145.00.--ISBN 3-527-29048-6
added in proof’, bringing the book as upM. Rosenblum’s book Cliemistrj. of to-date as possible by including references
Iron Group MerulloceneJ was published in to publications appearing up to about August 1994. The resulting total number of
1965. Now, just 30
references is around 2000. greatly easing
the task of finding one’s way into the primary literature.
However, in Chapter 6, “Macrocycles
and Cryptands Containing the Ferrocene
edited by A. Togni
Unit” (C. D. Hall), the reader will suffer
and T Hayashi. In
some disappointment, as this chapter
this monograph the
compares poorly with the rest of the book.
editors have set out
First one notices that the layout of the
to cover the most
formula schemes is inconsistent, varying
important areas of
from page to page in size, quality, and line
research in which
ferrocenes play a major role, and to ex- thickness. On two successive pages a otend and update the material in the ten donor bond between sulfur and a metal
volumes of the Gmelin Handbook devot- ion is represented variously by a dashed
ed to ferrocenes, and in the annual reviews line, a full line, and an arrowed line. Elsewhere ferrocene is shown as an iron atom
of ferrocenes research in the Journal of
between two cyclopentadienyl rings (repOrganomerallic CI7emistry.
The book is divided into three parts: I. resented by cpd) with no connection at all.
Homogeneous Catalysis, 11. Organic Syn- On closer inspection one notices that
thesis-Selected Aspects, and 111. Materi- about 50% of the structural formulas in
als Science. Chapter 1 of Part I (K.-S. this chapter are identical with the diaGan and T. S. A. Hor) describes the coor- grams in a recent review article by P. D.
Beer (Adv. Inorg. Cliern. 1992, 39, 79dination chemistry and catalytic properties of 1,l‘-bis(dipheny1phosphano)ferro- 157). This becomes painfully obvious
cene, and in the second chapter T. when small errors in symbols or in reproHayashi continues this theme by describ- duction in Beer’s review reappear at exactly the same positions in this chapter.
ing the use of chiral ferrocenylphosphanes
for asymmetric catalysis. Hayashi sets out But worse still. a detailed reading reveals
clearly and concisely the reasons why chi- that this copying is not confined to the
ral ferrocenylphosphanes are so impor- formula diagrams, as some passages of
tant as catalysts and inductors in organic text seem to have been reproduced from
ample) or to a third NMR-active nucleus
(e.g. ”F. 31P,or a suitable metal nuclide).
In Chapter 11 G. E. Martin and R. C.
Crouch describe examples in which the
structures of natural products and compounds of pharmaceutical importance
have been determined. These authors indicate that by using a microprobe head it
may be possible to further reduce the
amount of sample needed for an N M R
analysis. They show examples of reverse
2D N M R spectra obtained with 10 pg
samples in reasonable measurement
Lastly there is a glossary explaining
nearly 300 of the acronyms that are so
beloved by N M R spectroscopists. This
book can be thoroughly recommended.
Jiirgen Lauterwein
Organisch-chemisches Institut
der Universitiit Miinster (Germany)
the above-mentioned article with only minor changes, and without acknowledging
the source. For example, this is clearly
seen in Section 6.4.2, which has only been
very slightly altered and contains the same
literature references in exactly the same
But these serious criticisms of Chapter 6 must not be allowed to give the impression that the style is typical of the
book as a whole. On the contrary. the other authors‘ contributions are flawless and
are convincingly presented. Chapter 7 (P.
Zanello) gives a thorough account of the
electrochemistry and structural characteristics of ferrocenes, and includes an extensive tabulation of redox potentials.
Part 111 of the book, with the highly topical title “Materials Science”, describes the
many different aspects of ferrocenes as
materials. ranging from charge-transfer
complexes and magnetic materials (Ch. 8,
A. Togni) through liquid crystalline
compounds (Ch. 9, R. Deschenaux and
J. W. Goodby) to organometallic polymers (Ch. 10. K. E. Gonsalves and X.
Chen). These three chapters are especially
enjoyable to read. as they afford a glimpse
beyond the world of synthetic chemistry.
After reading Ferroceiies it seems well
justified to regard ferrocene as the
organometallic counterpart of benzene in
organic chemistry; this viewpoint helps
one to understand why the range of topics
treated in this book is so broad. On the
other hand, this wide-ranging character
might be seen by some readers as a disadvantage, because the ferrocene chemist,
for whom this book with its wide coverage
would be of greatest interest, does not really exist as such, and the individual chapters are more orientated towards the specialist. Nevertheless. this is a good book,
and for that reason especially it is unfortunate that the high price is likely to restrict
its effective market mainly to libraries and
the above mentioned specialist.
Herbert Plenio
Institut fur Anorganische
und Analytische Chemie
der Universitat Freiburg (Germany)
The Chemistry of the Fullerenes. By
A . Him&. Thieme, Stuttgart, 1994.
203 pp., paperback DM 80.00.ISBN 3-13-136801-2
About ten years after the discovery of
the fullerenes, and five years after they became available on a preparative scale, this
book by A. Hirsch now gives us for the
first time a well-written survey of the
rapidly evolving chemistry of this new
allotropic (and molecular) form of carbon. The book covers the most important
published work up to about the beginning
of 1994, lucidly summarizing the results in
nine chapters.
Thc first chapter gives a brief outline of
the discovery of the fullerenes. The author
describes the methods for preparing and
isolating some important fullerenes and a
few of their endohedral derivatives, and
briefly discusses their structure and spectroscopic properties. Chapter 2 is concerned with reduced forms of fullereneC,,,,. which arc of special interest because
ol' thc extraordinary solid-state (superconducting) properties of alkali metal fullerides. Chapter 3 deals with nucleophilic
addition of' carbanions, amines, and hydroxide ions to fullerenes-C,,, and -C,o.
Special attention is given here to the important problems of regioselectivity. the
initial step i n additions to C7,,,and multiple additions to the highly symmetrical
C,,,. Chaptcr 3 is devoted to the important organic cycloaddition chemistry of'
C,,,. with ;I lucid treatment of [4 21-,
[3 + 21-, [2 + 21-, and [2 + I]-cycloaddition reactions and the resulting products,
as well as the possibilities for further functionalization of these fullerene derivatives. Chapter 5 is concerned with the
hydrogenation of C,, and C,, , The available data on the many structural variations of constitutionally isomeric hydrogenation products and on their relative
stabilities are systematically reviewed and
are discussed from a theoretical standpoint. Chapter 6 discusses single and
multiple additions of organic and
organometallic free radicals to c,, , and
the free radical-initiated formation of
dimers and polymers. Chapter 7 deals
with complexes formed by fullerenes with
transition metals. Single and multiple additions of this kind can show considerable
selectivity, and structural factors influencing this are briefly discussed. Chapter 8
discusses the complex oxygenation and
oxidation chemistry of C , , and C,,, as
well as reactions with halogens and other
electrophiles. A separate section in this
chapter is devoted to the pioneering work
on the functionalization of fullerenes using osmium tetroxide. In the final chapter
the author summarizes the general features of the reactive properties of C,, and
C j , , and considers likely future developments in the chemistry of fullerenes (e.g.
multiple addition products with controlled constitution. heterofullerenes, endohedral fullerenes) .
This easily readable book gives an excellent insight into the still very rapidly
developing chemistry of the fullerenes. It
is mainly intended for chemists and materials scientists in academic and industrial
laboratories, and provides ;I good coverage of the original literature, including
much that is still novel and speculative. I t
is a highly valuable source of information
both for those already working i n the
fullerenes area and for newcomers. I recommend everyonc who wishes to learn
about the current state of knowledge in
fullerenes chemistry to buy this book.
H ~ ~ r r d z ~Kriiuiler
lnstitut fur Organische Chemie
der Universitiit Innsbruck (Austria)
Brian Kaye
Chaos & Complexity
Discovering the Surprising Patterns of Science and Technology
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