Reaction of N-haloamide. XXV. Addition reaction of N,N-di-bromobenzenesulfonamide with asymmetric olefins and .ALPHA.,.BETA.-unsaturated carboxylic acid esters.

Abstract

In order to confirm the orientation of the addition of N, N-dibromobenzenesulfonamide (DBBS) to olefins, the reactions of DBBS with asymmetric alkenes and α, β-unsaturated carboxylic acid esters were examined. The additions of DBBS to alkenes proceeded by Markownikoff's fashion, and those to the unsaturated esters gave the products which have bromines at α-carbons and sulfonamido groups at β-positions. The reactions of DBBS with 1-methylcyclohexene, 2, 3-dimethyl-1-butene, and 1, 1-dimethyl-1-butene gave I, III, and IV, respectively. The reactions of DBBS with methyl methacrylate, methyl acrylate, and methyl crotonate gave V and VI, VIII and IX, and XI and XII, respectively.