Mechanism of the reaction of vinyl acetate with phosphorus pentachloride

Abstract

1. We have studied the reaction of vinyl acetate with PC15 in CCl4 and benzene with reactant ratios of 1∶1 and 1∶2. A 1∶2 adduct is formed only at low temperatures (∼0°C) in a solvent that does not solvate it. More forcing conditions or conditions under which phosphorus chlorides are solvated form a 1∶1 adduct; this spontaneously isomerizes to the cyclic product of addition of PCl5 to two donor sites of vinyl acetate, which is catalytically converted to [2-(α,α-dichloroethoxy)-2-chloroethyl]phosphonic dichloride.