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Radical Anions of Polyalkylazulenes: An ESR and ENDOR Study

✍ Scribed by Rainer Bachmann; Clemens Burda; Fabian Gerson; Markus Scholz; Hans-Jürgen Hansen

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
555 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Proton‐hyperfine data are reported for the radical anions generated from azulene (1) and its alkyl derivatives 2–11 in 1,2‐dimethoxyethane both ‘chemically’ with K and electrolytically. The alkyl derivatives are 1,3‐dimethyl‐ (2), 5,7‐dimethyl‐ (3), 1,3,5,7‐tetramethyl‐ (4), 2‐methyl‐ (5), 4,6,8‐trimethyl‐ (6), 2,4,6,8‐tetramethyl‐(7), 1,3,4,6,8‐pentamethyl‐ (8), 1,3,4,8‐tetramethyl‐6‐propyl‐ (9), 6‐(tert‐butyl)‐1,3,4,8‐tetramethyl‐ (10), and 1,2,3,4,6,8‐hexamethylazulene (11). Alkyl substituents at the odd‐numbered centers μ = 1, 3, 5, and 7 partly shift the π‐spin population from the seven‐ to the five‐membered ring, whereas those at the even‐numbered centers μ = 4, 6, and 8 exert an opposite effect on the π‐spin distribution.

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