Reactions of Carbonyl Compounds in Basic Solutions. Part 31.1 The Effect of 2-Methylsulfonyl, 2-Methylsulfinyl and 2-Methylsulfanyl Substituents on the Alkaline Hydrolysis of Methyl Benzoate and Phenyl Acetate†

Abstract

Rate coefficients have been measured for the alkaline hydrolysis of methyl 2-methylsulfonyl-, 2-methylsulfinyl- and 2-methylsulfanyl-benzoates and 2-methylsulfonyl-, 2-methylsulfinyl- and 2-methylsulfanyl-phenyl acetates, as well as of the parent esters, in 30% (v/v) 1,4-dioxane–water at several temperatures: the relative rates of hydrolysis and the activation parameters indicate the importance of both polar and steric effects.