Electrochemical behavior of aromatic amines protected by the nitrobenzenesulfonyl group

作者: Maria V. Boldrin Zanoni , Nelson Ramos Stradiotto

DOI: 10.1002/ELAN.1140070412

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摘要: The electrochemical reduction of aniline protected by the 4-, 3-, or 2-nitrobenzenesulfonyl group in N,N-dimethylformamide (DMF) at a vitreous carbon electrode is reported. compounds are reduced three cathodic steps. first step about −0.85 V vs. SCE occurs with formation an unstable anion radical, which decomposes via NH bond cleavage. Reduction this sulfonamide −1.16 for para and meta isomers −1.48 ortho isomer. third higher potentials. BH cleavage always preponderant process. mechanisms discussed.

参考文章(16)
Margaret R. Asirvatham, M. Dale Hawley, Electrochemical studies of the formation and decomposition of p-nitrobenzenesulfonamide radical anions Journal of Electroanalytical Chemistry. ,vol. 53, pp. 293- 305 ,(1974) , 10.1016/S0022-0728(74)80142-7
Derek Pletcher, Nelson R. Stradiotto, The cathodic reduction of nosylate esters in dimethylformamide Journal of Electroanalytical Chemistry. ,vol. 186, pp. 211- 223 ,(1985) , 10.1016/0368-1874(85)85767-1
Maria Valnice Boldrin Zanoni, Nelson Ramos Stradiotto, The cathodic cleavage of the nitrobenzenesulfonyl group from aliphatic amines in N, N-dimethylformamide Journal of Electroanalytical Chemistry. ,vol. 312, pp. 141- 154 ,(1991) , 10.1016/0022-0728(91)85149-J
Allen J. Bard, Jaspal S. Mayell, Secondary reactions in controlled potential coulometry. II. Secondary electrode reactions The Journal of Physical Chemistry. ,vol. 66, pp. 2173- 2179 ,(1962) , 10.1021/J100817A023
Charles K. Mann, Peter T. Cottrell, Electrochemical reduction of arylsulfonamides Journal of the American Chemical Society. ,vol. 93, pp. 3579- 3583 ,(1971) , 10.1021/JA00744A006
H.L.S. Maia, M.J. Medeiros, M.I. Montenegro, D. Court, D. Pletcher, Deprotection by electrolysis Journal of Electroanalytical Chemistry. ,vol. 164, pp. 347- 361 ,(1984) , 10.1016/S0022-0728(84)80217-X
M.I. Montenegro, The electrochemical cleavage of protecting groups Electrochimica Acta. ,vol. 31, pp. 607- 620 ,(1986) , 10.1016/0013-4686(86)87027-X