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Book Review Ylid Chemistry. By A. W. Johnson

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sterism, end-product inhibition, isozyme, multienzyme complex) is missing from the index. “Enzyme induction” is
mentioned in the index, but the passage referred to is simply
the unsupported statement that “The adrenocortical hormones increase glyconeogenesis by true enzyme induction”.
Section C , which deals with “Formation, occurrence, and
importance in plants and microorganisms” (3 articles, 67
pages), concentrates o n the discussion of photosynthesis (47
pages). The only article on microorganisms, “Constituent
hydrocarbons of the bacterial cell” (20 pages), shows relatively little relation to glucose, but presents a well-rounded
account of this field, which is complex from the point of view
of structural chemistry. There is no general article on microorganisms, such as might be expected from the title of the
book. The 113 pages of Section B, “Methods of determination” (2 articles) will probably be the first pages of the library
copy to become grease-spotted and dog-eared; the material
in this section appears to be full and carefully written, with
a good understanding of the subject. We finally come to an
introductory chapter, “Chemistry and pharmaceutical chemistry”. This chapter presents a brief outline of carbohydrate
chemistry, in which the problems of conformation, which are
particularly important in connection with the enzymatic reactions of sugars, are dealt with in detail. The concebt of
instability factors and Hassel-Ottar and ,A2 effects a r e e i
plained with the aid of molecular models.
The air oxidation of D-ghCgSe to D-gluconolaolone is discussed as an “Inference from the conformational behavior”, and
is compared with the enzymatic oxidation of .glucose
phosphate. The example is i k h o s e n . Contrary to the statement that the enzymatic dehydrogenation “evidently depends on the axial position of the hydroxyl group on C-1 of
the a-glucopyranose” in the same way as the chemical hydrogenation, glucose 6-phosphate (like all aldoses) is in fact
enzymatically oxidized only in the form. The correct chemical parallel to this should therefore be oxidation with bromine, in which oxidation takes place at the equatorial hydroxyl
group of the form.
P
P
There is no doubt that this book contains a great deal of
valuable information that may be useful to anyone who is
concerned with the biochemical, physiological, and medical
aspects of sugars. However, just as a good memory depends
on storage capacity and ability to recall, so the value of such
a large handbook depends on whether the desired information,
which is assumed to be present, can be found quickly and
reliably. The index is not the best for ease of recall. This may
be the type of index that must be expected in the future when
indexes are compiled by machines. It is otherwise difficult to
understand e.g. why methylglucoside (pp. 24 and 25), a-Dmethylglucoside (pp. 22 and 58), ~-~-methylglucoside
(p. 22),
a-methyl-mglucopyranoside and P-methyl-D-ghcopyranoside (p. 106) are listed separately in the index, though the substances are simply anomers of the same compound. The last
two are given in English, since they occur in a n article written
in English. The German keyword “Gluconeogenese” is given
in 15 different contexts and with 26 page numbers. However,
none of these pages gives a clear definition mentioning the
main enzyme reactions o n which the phenomenon depends.
Nevertheless, this definition is given clearly and precisely in a
short section of an article written in English. To find this in
the index, one must look under “glyconeogenesis”, which
comes seven pages after “Gluconeogenese”.
What is “maltotriosyl”? It is an orthographic radical that
owes its existence to the English terminology (without covalent or coordinate bond?) in the phrase “which transfers
maltotriosyl residues”.
Nevertheless, the enthusiasm that filled the editor and the
authors and that led to the creation of this work is justified.
g glucose and related compounds form a family of imposing
might, which plays a n important part in all branches of
animate nature, and which must fascinate the specialists in
every phase of the development of our science.
K. WaIIenjels
[NB 585 IE]
Angew. Chem. internat. Edit. J VoI. 6 (1967) J No. 9
Laboratory Handbook of Toxic Agents. Edited by C. H. Gruy.
The Royal institute of Chemistry, London 1966. 2nd Edit.,
ix, 190 pp. Paperback 24s; 18s to Royal Institute of
Chemistry menbers.
The book comprises five sections: 1. General hazards involved
in the handling of chemicals (12 pages). 11. General precautions and accident prevention, including safe disposal of
chemicals (pp. 15-23). 1”. First aid in cases of skin-contact
and internal poisoning, including the different techniques
of applying artificial respiration (PO. 27-35).
IV. The main section (pp. 39-166): 250 toxic gases, reagents,
and solvents are listed in alphabetical oder (Acetaldehyde to
Xylidine). The acute and chronic sings of poisoning are listed
in a few key phrases for each substance, as are first aid
measures, the TLV(MAC) value, and the necessary warning
labeling. Each substance has about half a page devoted to it.
Synonyms are referred back to the appropiate passages under
their ‘approved’ names. Occasionally the nomenclature (in
the absence of formulae) is difficult to understand for German
readers, e.g. ‘methyl chloroformate’ ; ‘ethyl chloroformate’
at least has ‘ethyl chlorocdrbonate’ appended In parenthsis.
Chapter V (pp. 169-188) deals with the precautions to be
taken during handling of radioactive materials, and contains
I4 literature reference$
The book attempts to ahow. how careful handling of chemicals
can prevent accldents-and when these occur, how further
chanage can be @Voided.A page prefaced to the text is to be
filled in by the user with the name of the deputy safety
officer, the nearest hospital for casualties, ambulance, doctors, and persons trained to give artificial respiration, as well
as telephone numbers of poison information centers. The
glossary on the two concluding pages is evidently intended for
chemical laboratory workers, in that it explains simple
medical terms such as anemia, leukemia, bronchitis, urticaria,
etc. Unfortunately the book has no index.
The toxicological data contain mistakes - despite the collaboration of Ethel Browning. Thus fluorinated hydrocarbons
are described as liver poisons but not so chloroform. N o
warning of the increase in the potency of alcohol intoxication
following exposure t o aniline and nitrobenzene is given,
though this is a n important matter for the layman. The book
is suitable for obtaining rapid information about potential
risks by all those who understand English nomenclature.
H . Oettel
[NB 634 IE]
Ylid Chemistry. By A . W. Johnson. Organic Chemistry, Vol. 7.
Academic Press, Inc., New York London 1966. 1st Edit.,
x, 388 pages, numerous figures, bound S 12.50.
The Tower of Pisa leans because the ground subsided while
it was being built. Similarly, the structure of organic chemistry, which is built on the three pillars of carbonium-ion
chemistry, free-radical chemistry, and carbanion chemistry,
cannot be regarded as safe so long as the last of the three
pillars is weaker than the other two. This weakness is obvious from textbooks of organic chemistry.
To learn about the theoretical and practical importance of
carbanion chemistry, one must turn to special books. A new
addition to the ranks of such books is the present work o n
ylid chemistry by A. W. Johnson, who is himself a successful
investigator in this field, and has presented a comprehensive
picture of its development and its present state.
The author condehtrates o n the phosphorus ylids, which
have been. and still me. int,ensite]y studied because of their
preparative importance The bonding in these compounds,
which are formed by removal of a n a proton atom the phosphonium cation (onium complex), 1s eriticzfiy examined o n
the basis of their physical properties and reactivities. Further
chapters are devoted to the olefination ofcarbonyl compounds
and to the iminophosphoranes. This is followed by a discuss-
817
ion o f the nitrogen ylids including the pyridinium betaines
and diazo compounds; their rearrangements and their role in
the Hofmann degradation are interpreted. The book unfortunately does not contain a chapter o n the synthetic importance of this class of compounds, which opens up a new
route to phenanthrenes, cyclopolyenes, and isoindoles. The
As and Sb ylids, on which relatively little experimental work
has been done, are then discussed. The book closes with a
long chapter on sulfur ylids, which have attracted special
interest as valuable preparative aids. No mention is made of
the boron ylids, the study of which is still in its early stages;
these are formed by the removal of an a-hydride from ate
complexes, and their charge is opposite to that of the types
mentioned above.
The reader gains the impression that the ylids and cryptoylids have opened up a field of carbanion chemistry that
still conceals a wealth of theoretical and preparative problems
inviting further study. The book is strongly recommended to
organic and inorganic chemists involved in fundamental
research, particularly in the organometallic field.
G . Wirrig
[NB 614 IE]
Registered names, trademarks, etc. used in this journal, even without specific indication thereof, are nor t o be considered unprotected by law.
0 Verlag Chemie,
GmbH., Weinheim 1967.
- Printed in Germany
by Druckerei Winter, Heidelberg.
All rights reserved. No part of this journal may be reproduced in any form whatsoever, e.g. by photoprint, microfilm, o r m y other means, without
written permission from the publishers.
Editorial office: Ziegelhluser Landstrasse 35, 6900 Heidelberg, Germany, Telephone 24975, Telex 4 6 1855 kemia d, Cable address: Chemieredaktion
Heidelberg.
Editor: H. Griinewald . Translation Editors: A. J . Rackstraw and A . Stimson.
Publishers: Verlag Chemie GmbH. (Presidents Jiirgen Kreuzhage and Hans Schermer), Pappelallee 3, 6940 Weinheim/Bergstr., Germany. and
Academic Press Inc. (President Walter J. Johnson), 11 1 Fifth Avenue, New York 3, N. Y., USA, and Berkeley Square House, Berkeley Square,
London. W. I., England.
Correspondence concerning advertisements should be addressed to Verlag Chemie, GmbH. (Advertising Manager W . Thiel), Pappelallee 3,
6940 Weinheim/Bergstr., Germany, Telephone Weinheim 36 35, Telex 4655 16 vchwh., Cable address Chemieverlag Weinheimbergstr.
818
Angew. Chem. internat. Edit. 1 Yo[.6 (1967)1 No. 9
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