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Reactions of N-Methyl-N-Nitrosotoluene-P-Sulfonamide (Mnts) With 3,6-Dibromo-Carbazole and Its Corresponding Nitranion

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Reaction of N-methyl-N-nitrosotoluene-p-sulfonamide (MNTS, 1) with 3,6-dibromocarbazole (2) in dry acetonitrile gave N-methyl-p-toluenesulfonamide (4) and N-nitroso-3,6-dibromocarbazole (5), whereas with the corresponding nitranion (3) gave N-(p-toluenesulfonyl)-3,6-dibromocarbazole (6). The results are rationalized in terms of direct nucleophilic substitution mechanism occurring on respective sites. The effects of solvents and added metal ions are also discussed.

Affiliations: 1: Department of Chemistry, Nankai University, Tianjin 300071, CHINA


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