Elimination-addition. Part XVII. Elimination pathways in derivatives of β-sulphonylsulphonic acids

Abstract

In reactions of alkyl esters of 2-p-tolylsulphonylethanesulphonic acid with alkoxides, elimination of the p-tolylsulphonyl group occurs to a greater extent than the competitive elimination of the alkoxysulphonyl group; the difference is attributed to the greater activation of elimination by the alkoxysulphonyl group. Both products of elimination undergo addition of alkoxide.

2-p-Tolysulphonylethanesulphonyl chloride reacts with piperidine to give the piperidide in high yield but a small amount of sulphinic acid resulting from elimination is also obtained. In reactions with alkoxides the sulphonyl chloride gives the alkyl esters when equimolecular proportions of the reagents are used. With excesses of alkoxides, the product distributions are very similar to those found with the esters, showing that very little direct elimination occurs in reactions of the chloride.