New reactions of fluoroepoxides. Cleavage by trialkyl phosphites

Article abstract of DOI:10.1016/S0022-1139(00)80854-4

Mono-, di- and tri-substituted fluorine-containing α-oxides have been shown to enter into reactions with trialkyl phosphites which proceed through cleavage of the C-C and C-O bonds in the epoxide ring.The trialkoxyphosphorus ylides II, V, VII and VIII were obtained from the epoxides I, IV, VII and XVI.Triethoxyfluorocarbonylfluorophosphorane (IIIb) has been isolated and characterized.Further conversions of IIIb have been studied and the formation of trialkoxyphosphorus ylides XXIV containing a fluorine atom in the position α to the phosphorus atom has been noted.It has been shown that when propylene oxide reacts with triethyl phosphite, vinyl ethers are obtained through the intermediate formation of tetrafluoroethylidenetriethoxyphosphorane (XX).