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Application of 13C NMR to the study of the tautomerism of some disymmetric triazenes: The 3-aryl-1-(3,4-dimentyl-5-isoxazolyl)triazenes

✍ Scribed by G. Vernin; C. Siv; L. Bouscasse; J. Metzger; R. Faure; E. J. Vincent; C. Párkányi

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
413 KB
Volume
14
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^13^C NMR spectra of some 1,3‐diaryltriazenes, 3(1)‐aryl‐1(3)‐hetaryltriazenes and their methylated derovatives have been recorded. From the comparison of the ^13^C chemical shifts between 3‐aryl‐1‐(3,4‐dimethyl‐5‐isoxazolyl)triazenes 1 and compounds with fixed structure, such as 1‐aryl‐3,3‐dimentyltriazenes and methylated derivatives of 5‐amino‐3,4‐dimethylisxazole, we found that the triazenes 1 have the sturcture (A) in which the azo group is conjugated with the heterocycllic moiety. para‐Substituent on the aromatic ring have a week influence on the displacement of this tautomeric equilibrium. ^13^C NMR gives only qualitatives results. Theoretical calculation (HMO, CNDO‐2) are also consistent with the greater stability of tautomeric form A.

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