Studies on sulfenamides. XIII. Reaction of 2-nitrobenzenesulfenanilides with N-bromosuccinimide

Article abstract of DOI:10.1248/cpb.39.1857

The reaction of N-alkyl 2-nitrobenzenesulfenanilide (1a-3a) with N-bromosuccinimide (NBS) gave the corresponding monobrominated 2-nitrobenzenesulfenanilides (1b-3b) in good yields. The initial step of this reaction is the attack of NBS on the nitrogen atom of 1a-3a. The intermediate of this reaction is considered to be a cation radical of the sulfenanilides. A similar reaction of N-unsubstituted 2-nitrobenzenesulfenanilides (5a-10a) with NBS gave mono- or di-brominated 2-nitrobenzenesulfenanilides in low yields.

Full text of DOI:10.1248/cpb.39.1857

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