Nucleophilic reactivity. Part VII. The mechanism of hydrolysis of some unsaturated esters of methanesulphonic acid

Abstract

Allyl methanesulphonate gives the corresponding alcohol on alkaline hydrolysis, whereas the 1,4-dimethane-sulphonates of cis- and trans-but-2-ene give high yields of but-2-enal which is probably formed by a 1,4-elimination followed by alkaline hydrolysis at sulphur. The diesters give the substituted products only on reaction with the sodium salts of p-nitrophenol and thiophenol. The mode of activation of sulphonate esters by vinylic and acetylenic groups is briefly discussed.