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Book Review Molecular Biology of the Cell. By B. Alberts D. Bray J. Lewis M. Raff K. Roberts and J. D

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K
1,R=H
2, K = CH,
3,R=H
4, R = CH3
We now wish to report a novel reaction that a-diketones
undergo with CsK. Benzil 1 and&-dimethylbenzil 2 with
CaK afford phenanthrenequinone 3 and 3,6-dimethylphenanthrenequinone 4, respectively. This reaction. involves an intramolecular carbon-carbon bond formation.
The products are obtained in good yields and high purity,
while experiments with dispersed potassium under similar
conditions afforded only trace amounts of the respective
quinone. Graphite-potassium intercalate C8K is formed by
heating to 200°C potassium metal and dry graphite
(B.D.H.) with magnetic stirring[31.To freshly prepared CaK
(12.5 mmol in 20 mL dry THF), 2.5 mmol of benzil 1
(0.525 g, Fluka AG in 30 mL of THF) was added and stirred at room temperature (5 h, inert atmosphere). During
this period of time hydrogen gas evolves. The red reaction
mixture was quenched carefully with water and filtered,
extracted with CHzCI, and evaporated. Phenanthrenequinone 3 (3.7 g, 70%, m.p. 208°C(EtOH)[41was obtained.
Similarly, 3,6-dimethylphenanthrenequinone 4 was prepared from p,p’-dimethylbenzil in 72% yield (m.p. 216”C/
MeOH)[41.The same reactions can also be performed in
benzene or cyclohexane and the yields are 35% and 32%,
respectively[51.
This novel C-C bond formation reaction provides a
new synthetic pathway for the preparation of phenanthrenequinone-type compounds and their derivatives, especially in view of the easy affordability of substituted benzil
derivatives from the corresponding benzaldehydes.
The evolution of the hydrogen gas was followed and
measured. The rate of the gas evolution was found to be
constant. This observation may indicate that the process is
“layer-edge” controlled, i.e. the rate is determined by the
surface area of the graphite lattice which contains ordered
potassium atoms available for the reaction. This is consistent with the mechanism that we have previously described
for the bimolecular reduction of ketoneslZb1.The mechanistic behavior of C8K reactions with ketones, diketones and
their analogs is under further investigation.
Received: March 5, 1984 [Z 739 IE]
German version: Angew. Chem. 96 (1984) 594
[I] General reviews: (a) M. A. M. Boersma, Cat. Rev.-Sci. Eng. 10 (1974)
243: (b) A. McKillop, D. W. Young, Synthesis 1979, 401, 481; (c) R. Setton, F. Beguin, Synfhetic Metals 4 (1982) 299.
[2] a) M. Rabinovitz, D. Tamarkin, Synfhetic Commun., in press; b) D. Tamarkin, M. Rabinovitz, Synthetic Metals 9 (1984) 125.
[3] CsK was prepared in a modified procedure following the preparation of
Lallancette, see: J. M. Lallancette, G. Rollin, P. Dumas, Can. J . Chem. 50
(1972) 3058.
[4] Literature m.p. (3) 2O8-21O0C, (4) 212-213”C, from I. Heilbron: Dictionary ofOrganic Compounds, 5th ed. Chapman and Hall 1982, pp. 2197,
4570; C1 Mass Spectra and NMR Spectra (300 MHz) were identical t o
those of authentic samples.
[5] Conversion of benzil to phenanthrenequinone, catalyzed by AICI, with
low yields, was described by E. Abel, Eer. Dfsch. Chem. Ges. 55 (1922)
324.
Acknowledgement: We thank Dr. S. Zifrin of the laboratories of the Israel Police Headquarters for CI MS measurements.
BOOK R E V I E W S
Organotransition Metal Chemistry: Applications to Organic Synthesis. By S. G. Davies. Pergamon Press, Oxford 1982. x, 411 pp., bound, $ 85.00.
The use of transition metal complexes for the formation
of carbon-carbon bonds is not in itself new; the classical
investigations of Roelen and Reppe are nearly half a century old. Since then, however, the tremendous growth of
organometallic chemistry has opened up a variety of reactions that have greatly augmented the armory of the synthetically oriented organic chemist.
The author of the present monograph has aimed at acquainting the organic synthesis-oriented reader with the
possibilities of organometallic chemistry. The basic principles are dealt with in an introductory chapter, which, possibly because of space constraints, is so short that a list of
references for further reading would have been appropriate. A review of the synthesis of various types of complexes and methods of ligand elimination follows a section
concerned with the role of organometallic fragments as
protective groups and as stabilizing functions. The central
chapters deal with organometallic complexes as electrophilic and nucleophilic reaction partners; coupling and cyclization reactions, isomerization, redox and carbonylation
reactions are also described. Each section is provided with
a rich selection of literature examples. It is a pity that, nevertheless, such established reagents as organocopper compounds, which play such an important role in the formation of C-C bonds remain unmentioned-possibly because they are the subject of a recently published monoAngew. Chem. I n f . Ed. Engl. 23 (1984) No. 8
graph by G . Posner. In addition to established catalytic
processes, the main treatment is of stoichiometric reactions
that are seen as a potential basis for new synthetic methods. The literature is covered up to mid-1980. The majority
of the 700 references, which unfortunately are not without
error, stems from the last five years.
The same theme has been the subject of several monographs lately. Nevertheless, this book by Davies is a welcome addition. It is clearly set out according to mechanistic principles and is thus of value as a primary reference
source. It is well constructed from an instructional standpoint and gives a contemporary survey of the synthetic potentiality of organometallic chemistry. It will be of use to
all those who seek an “organometallic” solution of their
synthetic problems. Why this book, which is directly reproduced for the sake of topicality, is so expensive, is quite
another question.
Karl Heinz Dotz [NB 623 IE]
Anorganisch-chemisches Institut
der Technischen Universitat Munchen (FRG)
Molecular Biology of the Cell. By B. Alberts, D . Bray, J.
Lewis, M . Raff; K . Roberts, and J . D. Watson. Garland
Publishing, New York 1983. xxxix, 1142 pp., bound,
L 33.95.
This textbook, which has been written by a group of authors, deals with only one subject, the cell, from various
643
points of view, thereby abandoning the usual compartmentation according to subject. The cell is the building block
of all life. It is the host for subcellular life forms such as viruses and virus-like structures, it can also organize itself
into a supracellular assemblage, losing some of its autonomy. A cell is not a temporal or structural continuum, but
distinguishes itself by its functional complexity and its
ability to adapt to its surroundings. Differentiation can be
genetically programmed; it can, however, also be a response to environmental influences.
The first chapter of the book deals with the basic principles of cytology, by leading the reader from simple biomolecules up to multicellular organisms. The following section explains the techniques by which cellular structure
and functions are currently investigated. Even complicated
techniques such as cell fusion, the production of monoclonal antibodies, DNA cloning and cell sorting are explained in a very clear, albeit simplified, manner. The following chapter deals with the compartmentation of cells,
cell growth and cell division and with cellular communication. The last chapter is even more topical than its predecessors. This covers the topics of heredity, fertilization and
of cellular differentiation using the immune and nervous
systems as examples and last of all the molecular biology
of plants.
The individual contributions are written by specialists,
who quote material published in their field up to about the
end of 1982. The good didactic presentation and the courage to simplify are worthy of mention. Every contribution
has been checked by a second expert for its factual content
and comprehensibility. Each section ends with a summary
and short list of literature references.
The quality of the illustrations is superior even to that of
the text; for example, simplified schematic drawings are
almost always placed alongside electron micrographs. The
illustrations are not squeezed into the text on the principle
of maximum utilization of space but each individual page
is suitably graphically laid out even taking superscripts
and subscripts into account.
Which readership is this book suitable for? It is to be
recommended to each and every scientist in the fields of
education, biology, chemistry and medicine who wishes to
refresh and bring up-to-date his knowledge of cellular biology.
It is only suitable for students of biology or chemistry
after they have completed the first part of their undergraduate courses, since the biological facts in the text and illustrations are somewhat schematized. Since the quantitative
chemical-mechanistic aspect is neglected, the dominance
of the illustrations leads to an overemphasis of static structures.
All in all an excellent book, that is currently unsurpassed in content and production.
Hans Giinter Gassen [NB 627 IE]
Institut fur Organische Chemie und-Biochemie
der Technischen Hochschule Darmstadt
Advances in Polymer Science. Series,editors : H.-J. Cantow,
G . Dallilsta, K . Duiek, J . D . Ferry, H . Fujita, M . Gordon, G . Henrici-Olive, H . H. Kausch, J. P. Kennedy, W .
Kern, S . Okamura, S . Olive, C. G. Overberger, T. Saegusa, G . V. Schulz, W.-P. Slichter, and J . K . Stille. Springer-Verlag, Berlin. Vol. 54: Spectroscopy: NMR, Fluorescence, FR-IR. 1984. xi, 166 pp., bound, DM 98.00.ISBN 3-540-12591-4; Vol. 55: Solar Energy-Phase
Transfer Catalysis-Transport Processes. 1984. xi, 163
pp., bound, DM 98.00.-ISBN 3-540-12592-2; Vol. 56:
Anionic Polymerization. 1984. xi, 143 pp., bound, DM
98.00.-ISBN 3-540-12792-5; Vol. 57: Polymers in Medicine. 1984. xi, 168 pp., bound, DM 108.00.-ISBN 3-54012796-8
Specialist Periodical Reports. Amino Acids, Peptides and
Proteins. Vol. 14. A Review of the Literature Published
during 1981. Edited by J. H . Jones. The Royal Society of
Chemistry, London 1983. xxii, 478 pp., bound, E 73.00
(price reduction for members of the Royal Society of
Chemistry), total price for Vol. 1-14, E 294.00.-ISBN
0-85186-124-5
Photoelectron Spectroscopy. 2nd Edit. By J. H . D . Eland.
Butterworths, London 1983. 271 pp., bound, E 25.00.ISBN 0-408-71057-8
Specialist Periodical Reports. General and Synthetic Methods. Vol. 6. A Review of the Literature Published During
1981. Edited by G. Pattenden. The Royal Society of
Chemistry, London 19x3. xiii, 416 pp., bound, E 75.00
(price reduction for members of the Royal Society of
Chemistry), total price for Vol. 2-6: E 190.50.-ISBN 085186-874-6
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644
Angew. Chem. l n t . Ed. Engl. 23 (1984) No. 8
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