POLYFLUORO-1,2-EPOXY-ALKANES AND -CYCLOALKANES. PART III. SOME 1,2-EPOXIDES DERIVED FROM OLIGOMERS OF TETRAFLUOROETHYLENE

Article abstract of DOI:10.1016/S0022-1139(00)84973-8

Three oligomers (1>2>C=C3>) of tetrafluoroethylene, the trimer (R₁ = C2F5-; R₂ = R₃ = CF3-), the pentamer (R₁ = (C2F5)2(CF3)C-; R₂ = R₃ = CF3-) and the major hexamer isomer (R₁ = (C2F5)2(CF3)C-; R₂ = (C2F5)(CF3)(F)C-; R₃ = F) reacted with aqueous sodium hypochlorite/acetonitrile to give high yields of the corresponding 1,2-epoxides.Perfluoro-1-methyl-2(1-methylpropyl)cyclobutene (derived from the hexamer by pyrolysis) and perfluoro-4-ethyl-2,3,4,5-tetramethyl-4,5-dihydrofuran (made by hydrolysis of the pentamer) also underwent efficient epoxidation.The epoxy-oxolan decomposed in two ways at 280 - 480 deg C, one process giving the trimer of tetrafluoroethylene, probably by a radical pathway, and the other process, involving fluoride ion, affording tetradecafluoro-3,4-dimethylhex-3-ene-2-one.