Reactions of carbonyl compounds in basic solutions. Part 31. The effect of 2-methylsulfonyl, 2-methylsulfinyl and 2-methylsulfanyl substituents on the alkaline hydrolysis of methyl benzoate and phenyl acetate

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.