Studies on Sulfenamides. XII. : Anodic Oxidation of N-(o-Nitrophenylthio)-1,2,3,4-tetrahydroquinoline and N-(o-Nitrophenylthio)-1,2,3,4-tetrahydroisoquinoline

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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.
公益社団法人日本薬学会の論文
1986-10-25