The Reaction of Benzyl Arenesulfonate with N,N-Dimethylanilines (III). Substituent Effects of Leaving Group for Benzyl Arenesulfonate

Substituent effect of the leaving groups of the reaction of benzyl arenesulfonate with dimethylanilines in acetone at was obtained with the following results. 1. Substituent effect of the leaving groups was not variable when changed from pyridine to N,N-dimethylaniline in nucleophile 2.In acetone, the Hammett constant of p-MeO of the leaving group was -0.35. 3. The weaker the nucleophilicity in dimethylaniline, the stronger the movement of electron from N to C, and the cleavage of the C0 bond in transition state proceeds.