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.
Research on Chemical Intermediates – Springer Journals
Published: Jul 7, 2009
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