ELECTROOXIDATION PRODUCTS OF METHYLINDOLES - MECHANISMS AND STRUCTURES

Electrochemical oxidation of 1-methylindole, 2-methylindole and 3-meth ylindole on a platinum anode in acetonitrile containing NaClO4 has bee n studied. In any case no polymeric deposit on the working electrode w as obtained. The identification of the obtained soluble products is de scribed and the mechanisms of formation are discussed, Analogously to the case of unsubstituted indole, electrooxidized 1-3 react through po sitions 2 and 3. The non polymerization of 1 is explained with the for mation of a tetramer which is oxidized to a stable radical cation and dication without undergoing further coupling reactions. Copyright (C) 1996 Elsevier Science Ltd