Nucleophilic Substitution at a Carbonyl Carbon Atom (). Nucleophilic Substitution Reactions of N,N-Disubstituted Carbamoyl Chlorides

[摘要] Kinetic studies have been carried out on solvolyses and halide exchanges (Cl-, Br-, I-) of N,N-dimethyl-, N,N-diethylcarbamoyl chlorides, and solvolyses of N,N-diphenylcarbamoyl chloride. Kinetic results together with simple MO analysis indicated that: (a) N,N-dialkylcarbamoyl chlorides reacted via the SN2 mechanism, while N,N-diphenylcarbamoylchloride reacted via the SN1 mechanism; (b) in chloride exchanges, the bond-breaking appeared to be important, whereas in bromide and iodide exchanges, the bond-formation was shown to be important.

[学科分类] 化学（综合）