Electroorganic reactions. Part 56: Anodic oxidation of 2-methyl-and 2-benzylnaphthalenes: factors influencing competing pathways

JHP Utley, GG Rozenberg

Index: Utley, James H.P; Rozenberg, Gregor G Tetrahedron, 2002 , vol. 58, # 26 p. 5251 - 5265

Full Text: HTML

Citation Number: 34

Abstract

A systematic investigation of the anodic oxidation in nucleophilic media of 2-methyl and 2- benzylnaphthalenes, substituted at the 6-position in the naphthalene nucleus and at the 4- phenyl position of the benzylic side chain, has been carried out to identify factors favouring side-chain substitution. Cyclic voltammetry confirms that 6-substitution has a profound effect on the oxidation potentials of the naphthalene nucleus and 13C chemical shifts indicate ...