Neighboring Group Effects in Phosphonate Ester Hydrolysis, I. Neighboring Carbonyl Group in Paranitrophenyl Phenacyl Methylphosphonate

摘要

Kinetic studies on the alkaline hydrolysis of p-nitrophenyl phenacyl methylphosphonate, 1-anthraquinonyl p-nitrophenyl methylphosphonate, and ethyl p-nitrophenyl methylphosphonate were carried out. The results clearly demonstrate the participation of the neighboring carbonyl group in markedly accelerating the alkaline hydrolysis of selected methylphosphonates. Mechanisms are offered as possible explanations of the rate of enhancement. (Author)