Studies on Sulfenamides. IX. Anodic Oxidation of N-(o-Nitrophenylthio) alicyclic Amines

Abstract

Cation radicals generated by anodic oxidation of N-(o-nitrophenylthio) alicyclic amines (morpholine (1), thiomorpholine (tetrahydro-4H-1, 4-thiazine) (2), piperidine (3), pyrrolidine (4)) in acetonitrile were studied by cyclic voltammetry (CV) and electron spin resonance spectroscopy (ESR). 2-(o-Nitrophenylthio) indan-l-ol (6) was obtained from the solution after controlled potential electrolysis (CPE) of 1-3 in acetonitrile containing indene (5) and 0.1 M NaClO₄ at a glassy carbon anode. The cation radicals produced by CPE of 1-3 attacked 5 to give 6 as a final product.