Kinetics and Mechanism of the Pyridinolysis of N-Methyl-N-Phenyl Carbamoyl Chlorides

초록

A general consensus is that solvolysis of N,N-disubstituted carbamoyl chlorides proceeds primarily through an SN1 mechanism, which is favored by a strong electron delocalization from nitrogen. In contrast, for the aminolysis reactions of N,N-disubstituted carbamoyl chlorides, an SN2 mechanism was often suggested to apply. In this work, we investigated the reactions of N-methyl-N-phenylcarbamoyl chlorides with pyridines in dimethyl sulfoxide, and the mechanism for the dicussed in terms of the derived cross-interaction constants, ρXY.