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

Bewick Alan | Zendy; Edwards Gary J. | Zendy; Mellor John M. | Zendy

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

Author(s) -

Bewick Alan,

Edwards Gary J.,

Mellor John M.

Publication year - 1978

Publication title -

justus liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0075-4617

DOI - 10.1002/jlac.197819780105

Subject(s) - hexamethylbenzene , chemistry , coulometry , acetonitrile , linear sweep voltammetry , anodic oxidation , electrochemistry , anode , voltammetry , electrolyte , supporting electrolyte , cyclic voltammetry , platinum , inorganic chemistry , photochemistry , electrode , organic chemistry , benzene , catalysis

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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