
%0 Journal Article
%A Meisters, A 
%A Swan, JM 
%T Organophosphorus compounds. VI. The 'abnormal' Michaelis-Becker reaction. Diethyl 1-phenylepoxyethylphosphonate and diethyl 1-phenylvinylphosphate from diethyl phosphonate and phenacyl chloride
%J Australian Journal of Chemistry
%D 1965/02/01
%V 18
%N 2
%P 168-172
%K 
%R https://doi.org/10.1071/CH9650168
%U https://www.publish.csiro.au/paper/CH9650168 
%X Phenacyl chloride reacts with sodium diethyl phosphonate in liquid ammonia solution to yield a 7 : 3 mixture of diethyl 1-phenylepoxyethylphosphonate (Ia) and the isomeric diethyl 1-phenylvinyl phosphate (IIa). Reaction of phenacyl chloride with diethyl phosphonate and triethylamine in benzene gives only diethyl 1-phenylvinyl phosphate.   The action of hydrogen chloride on the epoxide (Ia) gives diethyl 2-chloro-1-hydroxy-1-phenylethylphosphonate (IV). This chlorohydrin reacts with sodium amide in liquid ammonia or with sodium hydroxide in ethanol to again yield a mixture of (Ia) end (IIa); with triethylamine in benzene, the product is mainly the vinyl phosphate (IIa). 
