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Anodic Oxidation of Hexamethylbenzene.Anodic Oxidation of Hexamethylbenzene in the Second Voltammetric Wave

✍ Scribed by Bewick, Alan ;Edwards, Gary J. ;Mellor, John M.

Publisher
Wiley (John Wiley & Sons)
Year
1978
Weight
627 KB
Volume
1978
Category
Article
ISSN
0074-4617

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✦ Synopsis

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 hydrocarbon is discussed on the basis of product studies, in situ specular reflectance spectroscopy, linear sweep voltammetry, analysis at a rotating disc electrode and by controlled potential coulometry. The minor oxidation product N‐(2,3,4,5,6‐pentamethylbenzyl)acetamide (5) is formed by reproportionation between a more highly oxidised species and 1. Application of anodic difunctionalisation to other methylbenzenes is discussed.

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