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

RF Hudson, RJ Withey

Index: Hudson,R.F.; Withey,R.J. Journal of the Chemical Society [Section] B: Physical Organic, 1966 , p. 237 - 240

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Citation Number: 4

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 ...