Synthesis of new α-hydroxy-, α-halogeno- and vinylphosphonates derived from 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

Abstract

Several α-hydroxyphosphonates have been prepared by the Pudovik reaction of the cyclic phosphite 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one with aldehydes and β-oxo aldehydes. These can be readily converted to α-chloro- or α-bromophosphonates in excellent yield by simply treating them with thionyl chloride or bromide. Reaction with phosphorus triiodide gave α-iodophosphonates and α-hydridophosphonates. The Pudovik products obtained from β-oxo aldehydes can be readily dehydrated to give vinylphosphonates.