Anodic oxidation of o-nitrophenylthioiminocycloalkanes.

Abstract

Two-electron anodic oxidation of o-nitrophenylthioiminocyclopentane(I) in methanol, followed by nucleophilic attacks of solvent and water (the latter present as an impurity in the solvent), gave methyl sulfinate and cyclopentaneimine. On the other hand, one-electron oxidation of o-nitrophenylthioiminocycloalkanes (1-6) in acetonitrile followed by deprotonation of the cation radical (B) gave the neutral radical (C), which then gave the thiyl radical (E). The rest of C reacted with E to give N,2-bis(o-nitrophenylthio) iminocycloalkanes, whose oxidation gave the final products (9-14). The results of cyclic voltammetry of 1-6 also show that the initial steps of anodic oxidation of 1-6 in acetonitrile and in methanol are one- and two-electron oxidations, respectively