Reaction of N-Haloamide. XXIV. N, N-Dibromo-o-carbomethoxybenzene-sulfonamide as a Reagent for the Preparation of β-Substituted Amines from Olefins

抄録

N, N-Dibromo-o-carbomethoxybenzenesulfonamide (1) was allowed to react with cyclohexene and styrene to give trans-2-bromo-1-o-carbomethoxybenzenesulfonamidocyclohexane (2) and 1-phenyl-1-o-carbomethoxybenzenesulfonamido-2-bromoethane (5), respectively. Compound 2 was converted to its aziridine derivative (3). It was found that the hydrolysis of 2 with 10% HCl-AcOH gave β-chloroamine which was converted to benzene-sulfonyl derivative 4. When 5 was treated under the same condition, formation of corresponding β-chloroamine, which was identified as its benzenesulfonamide 6, was observed. On the other hand, the treatment of 5 with base followed by the hydrolysis gave the amino alcohol 8, whose substitution pattern was different from that of 6, by way of the aziridine 7.