Abstract

Perfluorinated epoxides have been prepared primarily by the oxidation of the parent fluoroolefin. They readily react with nucleophiles to give ring-opened products and oligomers. Reactions with electrophiles also result in the opening of the epoxide ring. Perfluoroepoxides which contain a CF₂ linkage in the epoxide ring undergo smooth decomposition at modest temperatures to give difluorocarbene.

Hexafluoropropylene epoxide is the most important of this class of compounds. Its primary use is as an intermediate for the preparation of a number of commercially important trifluorovinyl ethers. The compound also serves as a starting material for the preparation of hexafluoroacetone and a series of oligomers which have been converted to a variety of stable liquids.

The chemistry of other perfluorinated epoxides, as well as that of epoxides containing small amounts of other halogen and hydrogen, has been explored. With the possible exception of the epoxides of perfluoroallyl chloride and tetrafluoroethylene the work is primarily of scientific and academic interest. The reactions are almost entirely analogous to those of hexafluoropropylene epoxide.