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Book Review Die Nomenklatur in der organischen Chemie (The Nomenclature of Organic Chemistry). By W. Holland

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Arrhenius parameters E, = 9.4 5 0.5 kcal/mole and log k =
12.9 i 0.3 for this rotational movement. This result can be
interpreted in terms of a certain degree of delocalization of
the spin density of the radical electron over the rest of the
molecule. / Z . Naturforsch. 24a, 1214 (1969) / -Hz.
[Rd 106 IEl
The molecular geometry of dmitrogen trioxide has been
determined by A . H .
A . p. ' O x , and R . .' Kuczkawski from the microwave Spectrum. The main difficulty
encountered in the measurements was that N203 is 99.5 %
dissociated to NO and NOz at the Pressures (lo-' to lo-'
torr) used in microwave SpeCtroscoPY, even at temperatures
as low as -78'C.
The spectra of Nz03 containing certain
percentages of 15N and 1 8 0 yield the following data: N2-N3 =
1.864 A; N2-01 = 1.142 A; N3-04 = 1.202 A; N3-05 =
1.217.A; 01-N2-N3
= 105.1O; 04--N3--N2
= 112.7';
of pyridine and benzenesulfonic acid) yields compound ( I ) ,
a derivative of the new ring system, m.p. 342-343 "C (DMF).
Compound (1) is ,-leaved by NaOCH3 to the ester (21,
regenerates ( I ) when heated to a temperature in excess of its
melting point. Several tautomers of ( I ) are possible. The NH
and the phenyl group could be exchanged. / Chem. Commun.
1969, 1040 i -Ma.
[Rd 111 IE]
A selective, stereospecific insertion of sulfur into olefins such
as norbornene has been described by T. C. Shields and A . N.
Kurtz. If sulfur is activated by NH3 or aniline in the presence
of an amide such as D M F as promotor and subsequently
heated to 110 O C with norbornene, 5-ethylidenenorbornene
A
h
H3C
,y@
------)
H
01,~--?1-~~-,04
N2 -N3 -+.-
H
(1)
'05
05-N3-N2 = 117.5 '. The molecule is planar; the frequency
of the twisting vibration about N2-N3 is 124 f 25 cm-1.
The dipole moment amounts to 2.12 D and acts in a direction
at 9.1 to N2-N3; the negative end of the dipole lies at the
nitro group. / Trans. Faraday SOC.65, 1963 (1969) / -Hz.
[Rd 109 IE]
H3C&>'
H
(4
( I ) , or similar compounds, ex0-3,4,5-trithiatricyclo[5.2.1.02~6]decane or the I-ethylidene derivative (2) is obtained in 86 or
71 % yield. up to 99 % DMSO or an
of amide can
serve as solvent. The addition occurs exclusively at the
double bond of the ring. J. Amer. chem. SOC. 91, 5415
(1969) /-Ma.
[Rd 112IEl
New luminescence experiments on azulene are the subject of a
report by p. M . Rentzepis. Azulene and its derivatives occupy
a special place among all organic compounds owing to the
fact that under normal conditions they only fluoresce from
the second excited singlet state. Excitation with extremely
short laser pulses (several 10-12 s) has now revealed emission from the first excited singlet state S1 (maximum at about
H
a
N
7
,
"
,
c
6
H
5
750 nrn)
and
the lowest
triplet state TI (maximum at about
11OOnrn). The fluorescence from S1 has a decay time less
than 10-10 s and a quantum yield of about 10-7. Phosphoco
I
NH2
rescence from TI could only be observed at 77°K with a
OCH,
decay time of 10-6 s. / Chem. Physics Letters 3, 717 (1969) ,I
(2)
-Hz.
[Rd 117 IE]
The triazino[2,1-b]quinaz0line system has been synthesized
for the first time by J. T. Shuw and J. Ballentine. The acidcatalyzed cyclization of K dicyanobenzamidine with methyl
anthranilate (refluxed in anhydrous methanol in the Presence
-'
NKNH
R y N , ' 6 ' 5
0
OCH3G_
NH
(1)
NYN
BOOK REVIEWS
d i e Nomenklatur in der organischen Chemie (The Nomenclature of Organic Chemistry). By W. Holland. Verlag
Harri Deutsch - Zurich-Frankfurt/M. 1969. 1st Edit.,
190 pp., stitched, D M 34.80.
As stated in the introductory remarks, the author set himself
the task, not merely of giving the nomenclature rules current
today, but also of describing the older usages. The book does
indeed contain numerous references to previous proposals
for, and usages in, nomenclature, so that the original iiterature can still be understood by the reader. However, as a guide
and help in the formation of names for organic compounds and that is what it should be- the book cannot be unreservedly recommended because of the various contradictions
it contains. For instance, on p. 46 methoxycarbonyl is correctly recommended in place of the older designation carbomethoxy, yet on p. 36 only carbobenzoxy (with the abbreviation Cbo) is given for the amino acid protecting group and
not benzyloxycarbonyl (with the abbreviation Z ) . In the
explanation of the ring fusion principle on pages 87-88
the instruction is recorded whereby the parent compound
shall chosen to be as large as possible and the anneland as
994
small as possible, but a contradiction to this is met on page 89
where in the explanation of numbering round the outer ring
the example naphth[2.1-a]anthracene should correctly be
named benzo[b]chrysene [RRI 63791. And the list of such
contradictions could be considerably extended. Also it is
not evident why in the tables aromatic compounds are drawn
sometimes with and sometimes without double bonds.
Ilse Spaeth [NB 837 IE]
Kunststoff-Handbuch, Band IV: Polyolefine (Plastics Handbook, Vol. 4: Polyolefins). Edited by R . Vieweg, A . Schley,
and A . Schwurz. Carl Hanser Verlag, Miinchen 1969.
1st Edit., mi + 976 pp.. 795 illustrations, 106 tables,
linen DM 270.-; on subscr. to the complete work (12 vol.)
DM 216.-.
The rate of production of polyolefins has grown faster than
that of any other thermoplastic, so that appearance of the
present volume[lI should receive a warm general welcome,
[11 Cf. Angew. Chern. 82, 542 (1969); Angew. Chem. internal.
Edit. 8, 468 (1969).
Angew. Chem. internal. Edit.
/ Vol. 8 (1969) / No. 12
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