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< 1) for Y = electron-withdrawing substituent. The proposed mechanisms of the benzylaminolyses of N-methyl-Y-α-bromoacetani-lides are a concerted mechanism with a five membered ring TS involving hydrogen bonding between hydrogen(deuterium) atom in N-H(D) and oxygen atom in C = O for Y = electron-donating, while a concertedmechanism with an enolate-like TS in which the nucleophile attacks the α-carbon for Y = electron-withdrawing substituents.Key Words :Benzylaminolysis, N-Methyl-α-bromoacetanilides, Cross-interaction constant, Deuterium kineticisotope effect, Biphasic nonlinear free energy correlationIntroductionIn a series of the nucleophilic substitution reactions ofα-halocarbonyl compounds,

Nucleophilic Substitution Reactions of N-Methyl α-Bromoacetanilides with Benzylamines in Dimethyl Sulfoxide