
TY  - JOUR
A1  - Meisters, A 
A1  - Swan, JM 
T1  - Organophosphorus compounds. VI. The 'abnormal' Michaelis-Becker reaction. Diethyl 1-phenylepoxyethylphosphonate and diethyl 1-phenylvinylphosphate from diethyl phosphonate and phenacyl chloride
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1965
VL  - 18
IS  - 2
SP  - 168
EP  - 172
KW  - 
UR  - https://doi.org/10.1071/CH9650168 
N2  - 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). 
ER  -

