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Book Review UV-Atlas organischer Verbindungen Band 1 Ц UV-Atlas of Organic Compounds Vol. 1

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powder that decomposes at about 280°C. If the reaction
with ( I ) is carried out at 0 ° C instead of at room temperature,
the product obtained is bis(3,5-di-t-butyl-4-hydroxyphenyl)cyclopropenone. On oxidation, this gives the violet ketone,
whose solutions decompose within a few hours to form the
red-purple compound (3). / J. Amer. chem. SOC.89, 152,153
(1967) / -Ma.
[Rd 654 IEI
phenyl-lithium under the conditions of the reaction. Thc
attack of aryl-lithium compounds on nitrobenzene (a&ainst
the polarization of the nitro group) also takes place exclusively at the oxygen, as was shown by experiments with phenyllithium or p-tolyl-lithium and p-nitrotoluene or nitrobenzene.
The course of this reaction has not yet been elucidated. ,'
Tetrahedron Letters 1967, 1563 / -Bu.
[Rd 665 IE]
A new berkelium isotope, ':;Bk, has been isolated by H. Diamend, R . K. Sioblom, R. F. Barnes, J. L. Lerner, D . J . Herderson, and P. R . Fields. T;Bk is formed by a-decay of y:ES,
2SSEsis present to the extent of0.01 to 0.001 % in 253E3s9which
is obtained by reactor irradiation of curium or californium.
251Bk is a emitter with a half-life of 57.0 = 1.7 min; 34 and
140 keV y radiation is also observed (94 and 184 keV ?'
radiation is probably also emitted). The absence of measurable y intensities at 58.5 and 81 keV suggests that the ground
state of :;Bk
is not 7,12 + [633], as might be expected by
analogy with 249Bk. / J. inorg. nuclear Chem. 29,601 (1967) /
-WG.
[Rd 703 IE]
One-step syntheses of pyrimidinethiones and pyrimidkedi~A . ill^^,
~
l
thiones have been described by E. c. ~
s. Komen, and R . Warrenel..These compounds are of pharmaceutical interest. The synthesis can be illustrated for the case
of (31, which was formerly obtained in an impure State and i n
low yields from the Same starting material ( I ) by a four-step
qcN
N\N
H
3h
H
,H
(2)
N=C,
OC2H5
S
The inverse addition of phenyl-lithium to nitrosobenzene to
give 0,N-diphenyl-N-lithiohydroxylamine( I ) has been
described by P. Buck and G . Kobrich. ( I ) could not be isolated, since it undergoes rapid nucleophilic substitution by
phenyl-lithium, with formation of lithium diphenylamide and
lithium phenoxide.
NaHS
10-12 h
H
synthesis. ( 3 ) is obtained in a thin-layer chromatographically
pure state and in 97% yield without isolation of the intermediate (2). Pyrimidinedithiones such as (5) are also obtain-
C6H,-N=O
C,II,L~
NH
H
'6135,
N-IJi
+ T,iOC6H5
(4)
C6Hj
The course of the reaction is shown by the fact that, apart
from deprotonation, N,N-diphenylhydroxylamine (which is
obtainable from nitrosobenzene and CGHSMgBr) is inert to
H
S
H
H
f5)
ed from ( I ) . The rearrangement of the thiazine (4) into (5)
(87 % yield) is a well-known base-catalysed reaction. / Tetra[Rd 666 IE]
hedron 23, 885, 891 (1967) / -Bu.
BOOK REVIEWS
UV-Atla9 organischer Verbindungen, Band 1 - UV-Atlas of
Organic Compounds, Vol. 1. Compiled by the Documentation of Molecular Spectroscopy (DMS). Verlag Chemie
GmbH., Weinhejm(-Bqp& and Butterworths, London
1966. 1st Edit., iv, 32 pages of text, 23 tables, 208 spectra,
ring book $ 20.00.
The present volume is the first of a planned five-volume UV
atlas, and provides some idea of the care that has been taken
In the planning of this work, which is ultimately to include
about 1000 spectra. The selection of the substances dealt
with is reflected in the following classification:
A.
B.
C.
D.
E.
Compounds with C-C multiple bonds.
Compounds with C = O and C=S groups.
Compounds with C-N multiple bonds
Mononuclear aromatic compounds.
Polynuclear aromatic compounds.
F. Aromatic compounds containing non-benzoid rings.
G. Mononuclear heterocycles.
H. Condensed heterocycles.
1. Saturated organic compounds.
5. Compounds o f biological interest.
Angew. Chem. internat. Edit. 1 Val. 6 (1967) 1 No. 9
K. Inorganic systems.
L. Spectrochemical substances.
M. Solvents.
For ease of comparison, all the spectra are printed on transparent paper and marked with a reference point. They can be
superimposed o n one another as desired, owing to the looseleaf form of the Atlas. The Flots are always linear in wave
numbers and logarithmic in the extinction coefficient. All the
spectra are provided with a wavelength scale, which saves
calculation. The graphical representations are supplemented
in mant' cases b y tables containing further data on the wave
numbers and extinction coefficients of the absorption maxima
of hOmOlOgous compounds, derivatives, or ions. After completion, the spectra of the principal groups (A)-(M) will be
discussed and interpreted by the editors-of the sections in
question.
The first volume contains 57 spectra and 13 tables for Group
D (editor: H . H . Perkampus), 132 spectra and 10 tables for
Group H (editor: S . F. Mason), and 19 spectra for Group M ,
which is accompanied by a six-page introduction by the
section editor B. Hampel, with valuable advice o n the purification of various solvents.
815
~
~
The first volume does justice to the promises of the prospectus. We look forward with interest to the early publication of
H . Lnhliort
[NB 611 I € ]
the later volumes[*].
[ * ] Editorial note: Volume 2 has now appeared. Volume 3 is
due to appear in September 1967 and Volumes 4 and 5 should
be available in January 196s.
Trivialnarnenkartei-1 .Erganzungslieferung (Card 1ndex ofTrivial Names - 1st Supplementary Issue). Verlag Chemie
GmbH.. WeinheimiBergstr. 1966. 1088 cards, DM 60.-.
In 1964, Verlag Chemie began to compile a card index of trivial names [I]. The first issue contained 8000 cards. Each card
bears a number giving its position in the alphabet, the trivial
name in question (in German on the left, in English on the
right), the structural formula of the compound with stereochemical details (where known), the empirical formula, and a
reference to a handbook or journal. It is explained that the
aim of this card index is not to foster trivial names, but to
provide information wherever none is supplied by the trivial
name. For example, it should be of assistance to anyone who
does not know what palustrinic acid Centaur X4, or munetone is. However, he should also possess the first supplementary issue, which contains to88 cards’and which has just been
published. It also contains a list of addenda to the cards of
the first issue
Further supplementary issues are plrlnne’d, and it is really
unnecessary\ro emphasize the vame of this card index. Those
who already have it at their diSbosal will have learnt to
treasure it, and those who do not yet know it should acquire
it as soon as possible for the sake of easy reading in chemical
literature.
H. Griinewald
[NB 581 IE]
[I] Cf. Angew. Chem. 78, 344 (1966); Angew. Chem. internat.
Edit. 5, 326 (1967).
Reactiones Organicae. Organische Reaktionen und Methoden.
(Organic Reactions and Methods.) By H. J. Ziegler. Georg
Thieme Verlag, Stuttgart 1967. Basic stock (12 batches):
about 3000cards; about 250cards per batch. Price per batch:
D M 220.-; 20% reductionwhen thecompleteworkisordered.
A greet deal has been done to classify chemical literature in
such a way that any desired information can be found quickly
and as fully as possible, but without padding. A new attempt
to make the knowledge of preparative organic chemistry
readily accessible is the card index entitled “Reactiones Organicae” that has been compiled by H. J . Ziegler. This index
contains all the procedures from “Organic Syntheses”, all
the reaction types from “Organic Reactions” and (with the
exception of the ring-closure reactions) from “Cahiers de
Synthese Organique”, and all the reactions from “Namenreaktionen der Organischen Chemie”. The basic stock contains 3000 cards. (Eight batches containing a total of 2000
cards have been issued so far.) It will be continuously
supplemented and updated by further batches.
The card index consists of punched cards, each of which
describes a reaction or asynthesis (sequence of reactions). In
the heading on the front of each’ card, the reaction type is
given on the left, the reaction conditions a n d reagents on the
right, and references t o Houben-Weyl and to “Cahiers” in
the center. In the field below the heading, the reaction described is characterized by a complete formula, data on
yields, and a Qterature reference. On the back of each card is
the name of the reaction prcduct, a short account of the
procedure in German and in English, and a list of compounds
(with yields) tlat can be prepared in the same way.
The “knack” of “Reactiones Organicae” is that any desired
reaction is first reduced to a reaction type. For example,
suppose that one wishes to find the possible methods for the
oxidation of secondary amines to azomethines. This reaction
can be represented in its simplest form by the equation
\
CH-NH-
816
\
+ ,C=N-.
Code numbers for the partial formula on the left (starting
group) and for that on the right (product group) are then
found from two formula indexes supplied with the cards
in the form of loose-leaf books. These numbers then enable
il selector instrument to extract all the cards that describe
such reactions. For more specialized problems, code numbers characterizing the reaction conditions and the overall
constitution of the product are available.
The entire system is both cleverly conceived and easy to use.
Aids (program blocks, color code) are provided to facilitate
further the use of the card index and to make it foolproof
even for assistants. The greatest advantage of “Reactiones
Organicae”, however, is the fact that no notation that is not
familiar to the chemist, no hypotheses on reaction courses,
and no classification of reactions are included, and that
neither nomenclature problems nor language problems arise.
Thus “Reactiones Organicae” is the ideal literature card
index for the organic chemist engaged in preparative work.
H. Griinewald
[NB 519 I€]
o-Glucose und verwandte Verbindungen in Medizin und Biologic (D-Glucose and Related Compounds in Medicine and
Biology). Edited by H. Bartelheimer, W. Heyde, and W .
Thorn. Ferdinand Enke Verlag, Stuttgart 1966. 1st Edit.,
xv, 1126 pp., 173 figures, 124 tables, cloth DM 228.-.
Contrary to what one might expect from its title and size,
this book cannot be summed up in the words “all about
glucose”. It is not a sort of monograph in which one can
quickly find out all about a certain chemical or biochemical
property of this sugar or of one of its derivatives, but is
rather a eulogy on this compound and its direct and indirect
biosynthetic transformation products and precursors. The
subject matter covered in the book is by no means narrow.
For example, it contains long chapters on “The oxidative final
stage of metabolism”, i.e. on the transformation of the transformation products of the products of transformation of Dglucose, on “The quantum chemistry of photosynthesis,
automatically written”, where only a few of the compounds
described are ultimately converted into or formed from
glucose or glucose derivatives. One could, if one were so
inclined, say that any carbon compound found in plant or
animal cells or in microorganisms is a potential precursor or
transformation product of D-glucose, provided that the
organism in question can use glucose as a source of carbon.
The editors are therefore forced to make a selection, unless
they wish to compile a “Beilstein” of natural products. The
question that arises now is whether the selection made was a
good one. Closer examination shows that is it impossible to
give any general answer; in the 45 chapters by 54 authors, the
problem of relatedness of the subject under discussion to
glucose is solved in various ways.
Almost half of the work is devoted to pharmacological,
pathophysiological, and clinical aspects. Several articles in
this part deal with the role of glucose in particular and/or of
hydrocarbons in general in disease and in the function of
various organs (endocrine disorders, diabetes mellitus,
kidneys, liver, heart, lungs, joints, brain, skin, eyes, throat,
nose, ears, tumors), in surgery, pediatrics, and psychiatry,
and in sport. These chapters offer a great deal of valuable
information to those with no medical training.
The general chemical and biochemical principles of these
special chapters are, unavoidably, not always in agreement
with the latest fundamental developments, which always
penetrate into the more specialized sectors of a science only
after a certain time lapse. Unfortunately, the same is also
true of many of the fundamental articles in Section D, “Biochemistry and Physiology” (283 pages).
The length of this time lapse will not be discussed for the
various articles. An average minimum value can be estimated
from the fact that almost the entire molecular biology vocabulary (e.g. induction, repression, operon, messenger, alloAngew. Chem. internat. Edit. Vol. 6 (1967)/ No. 9
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