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Book Review Synthesen mit Kohlenmonoxid (Syntheses with Carbon Monoxide). By J. Falbe

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made of the numerous figures and graphs. The various types
of reactors are discussed in Chapter 6, though the reviewer
would have expected a more detailed discussion of nuclearphysical principles (e.g. four-factor formula); however, this
is a shortcoming of all (even English-language) books on
radiochemistry and nuclear chemistry. Even physical principles are sometimes unfortunately not discussed at length;
there was no need to avoid mathematical formulations almost
completely. What the Friedlander-Kennedy-Miller book
lacks in chemistry, the Hecht book lacks in physics. One
would also have expected that in 1968 (the year of publication), the new position regarding the No isotope (dating
from 1963-1965) could have been presented; moreover, the
symbol Mv for element 101 (p. 241) was changed by the
IUPAC into Md almost ten years ago. These and other minor
points can, however, be corrected in a later edition.
The presentation and print are well below average, even if
allowance is made for the relatively low price. At least two
types of paper had been used in the reviewer’s copy, several
pages showed variation in print thickness or unsharp print,
and the paper binding delaminated after use for a short time,
so that the life of the book will probably be limited.
C . Keller
[NB 799 IE]
Synthesen mit Kohlenmonoxid (Syntheses with Carbon
Monoxide). By J. Fulbe. Vol. 10 in the Series “Organische
Chemie in Einzeldarstellungen”. Springer Verlag, Berlin,
Heidelberg, New York, 1967. 1st Edit., vii + 212 pp..
20 tables, D M 48.-.
Except for a few omissions, the author has succeeded in
writing a comprehensive monograph on syntheses involving
CO, and even experts in this field can find something new in
it. Hydroformylation, carbonylation. the Gattermann-Koch
synthesis, and carbonylation with Pd catalysts are described
in detail, irrespective of their technical importance. It is
obviously impossible in such a comprehensive book to
consider singly the entire literature quoted and to specify in
each case the importance of the individual works.
I t is mentioned in the Preface that, prior to their detailed
investigation, Reppe syntheses and Roelen reactions were
described after World War I1 in FIAT, BIOS, and CIOS
Reports. Despite this, workers engaged in the subsequent
intensive research in this field outside Germany hardly took
into account the previous investigations, with the result that
many aspects have been discovered twice. This could have
been brought to light still better by modifying the structure
of the book.
In connection with the reaction mechanisms, mention is
made again of the three-membered ring and ketene theory,
which was rejected years ago. On the other hand, only
footnotes are devoted to the important hypotheses proposed
a long time ago about the intermediates of hydroformylation
and carbonylation (FIAT, Houben-Weyl). At the same time,
a detailed account is found o n the mechanisms which were
proposed much later, and which closely resemble these
hypotheses.
This does not alter the fact that this is a very good book,
which can be recommended to those who work in this field.
H. Kroper
[NB 791 IE]
Comprehensive Biochemistry, Vol. 20: Metabolism of Cyclic
Compounds. By M. Florkin and E. H . Stofz. Elsevier
Publishing Co., Amsterdam, London, New York, 1968.
1st Edit., xiii + 533 pp., 135 figs., 34 tables; Dfl. 75.-.
This volume[l] deals with the biosynthesis and the degradation of complicated organic molecules arising in the metabolism of carbohydrates and amino acids. It bears witness to
111 Cf. Angew. Chem. 80, 974 (1968); Angew. Chem. internat.
Edit. 7, 901 (1968).
Angew. Chem. internat. Edit.
Vol. 8 (1969) No. 5
the great progress made in the last I S years in the elucidation
of structural relationships by new methods and improved
techniques. Not only is the literature well documented up to
1967, hut also a great number of quotations are included in
some cases. As a result, this book often makes it unnecessary
to consult the original articles for details. It also gives surveys
which enable the reader to familiarize himself with the
relevant material.
Discussing the isoprene derivatives, H . J . Nicholas describes
the synthesis, degradation, occurrence, and function of
vitamin A, a-tocopherols, vitamin K. ubiquinones, plastoquinone, carotinoids, squalene, and other terpenes, as well
as rubber. H e also discusses ecdysone and the giberellins,
together with their function and the regulation of the biosynthetic cycles between organelles. The metabolism of
steroid hormones and bile acids is discussed by D . B. Gorer,
whose account includes the formation and the conversion of
CIS, C19, and Cz1 sterols, the action of ACTH and other
hormones, the enzymatic hydroxylation and dehydrogenation
of the steroid skeleton, and processes of conjugation and
elimination. The author examines the reaction mechanisms
in great detail and also discusses the secondary conversion
of bile acids by intestinal microflora, though the products
of this conversion are only indirectly connected with biogenetic cycles.
The phenolic substances are divided into flavonoids (F. U‘P
Eds), tannins (D. G. Roux), and lignin (W. J . Schuberf),
which is biogenetically connected with tannins in carbohydrate metabolism. The glycosides and the aglycons of
flavones and flavonones are of pharmacologic interest, and
their toxicology and therapeutic use therefore receive critical
treatment. One finds a similarly good account of the influence of intestinal bacteria, nutritional factors, and dosage
on the products of metabolism and elimination. The hydrolyzable and condensed polyphenols of the tannins are
examined in a relatively short but informative section. Here
and in the chapter o n lignin, one encounters isocyclic polyhydroxy compounds, which occupy a central position in the
metabolism of aromatic systems, and which are aromatized
and - in the case of lignin - condensed into large, complex
polymeric molecules. Their chemical structure is mainly
hypothetical, and it is therefore too soon to discuss the
general features of these molecules. By contrast, the general
outlines of the biogenesis based on C02. carbohydrates, shikimic acid, and C3 fragments are known. The same applies to
the origin of methoxy groups and to the polymerization of
monomeric phenylacrylic acid precursors by enzymatic
oxidoreductase and peroxidase (laccase). The degradation by
fungi that decompose wood is first hydrolytic (even ether
bridges are cleaved here by etherases), and then oxidative,
leading to vanillin derivatives.
A monographic study of the biosynthesis of alkaloids and
other secondary nitrogen metabolites by J . E . Spenser represents the main part of the book. This subject is treated in
biogenetic terms, and, despite the great variety of the substances, the study shows the relations between the synthetic
pathways, which had been earlier proposed speculatively by
organic chemists, mostly exhibiting an extraordinary insight.
The syntheses involved are relatively simple (Mannich condensations and oxidative coupling of phenols), but give rise
to a remarkable group of compounds, which are difficult to
systematize.
One of the most fascinating chapters of the chemistry of
natural products is that of secondary fungal metabolism,
although the underlying principles are not clear since we do
not know whether we are dealing here with elimination
processes or with accumulation processes; nevertheless,
about 1000 compounds have so far been isolated. R . Bentley
and J. M. Campbell examine some routes for the aromatic
syntheses based on glycolysis intermediates, acetate, mevalonate, and polyoxomethylene compounds, together with the
formation of terpenes, sterols, and anthraquinones. The
enzymatic halogenation and the regulation of these processes
have also been described.
397
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