Abstract
The paramagnetic species formed by anodic oxidation of N-(o-nitrophenylthio)-1, 2, 3, 4-tetrahydroquinoline (3) in acetonitrile has been identified as the radical cation of 1, 1', 2, 2', 3, 3', 4, 4'-octahydro-1, 1'-di-(o-nitrophenylthio)-6, 6'-biquinoline by isolating the radical cation perchlorate. The perchlorate separated out from the electrolyzed solution and its structure was confirmed by converting it to 1, 1', 2, 2', 3, 3', 4, 4'-octahydro-6, 6'-biquinoline. Anodic oxidation of N-(o-nitrophenylthio)-1, 2, 3, 4-tetrahydroisoquinoline (4) in methanol gave an almost quantitative yield of 3, 4-dihydroisoquinoline (7) and a 56% yield of methyl 2-nitrobenzenesulfenate (9). In acetonitrile, electrolysis of 4 gave a 33% yield of 7 and no 9. These results were interpreted in terms of a much faster rate of deprotonation of the sulfenamide radical cation in methanol than in acetonitrile.
