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On the gearing of methyl groups in hexamethylbenzene

✍ Scribed by Linda D. Iroff

Book ID
102306217
Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
387 KB
Volume
1
Category
Article
ISSN
0192-8651

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✦ Synopsis

Abstract

Empirical force field calculations were performed on hexamethylbenzene to elucidate the internal motions of the methyl groups. When the benzene ring is constrained to be planar (as in solid‐phase studies), the methyl groups undergo a geared, disrotatory motion. When this constraint is relaxed, results are force field dependent. Calculated barriers are in good agreement with experimentally determined values.

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## Abstract Anodic oxidation of hexamethylbenzene (**1**) in acetonitrile with Bu~4~NBF~4~ as electrolyte at a platinum anode at +1.7 V (versus Ag/0.01 M Ag^+^) gives mainly 1,3‐bis(acetamidomethyl)‐2,4,5,6‐tetramethylbenzene (**6**). The mechanism of this electrochemical difunctionalisation of a h