Polyfluoro-1,2-epoxy-alkanes and -cycloalkanes. Part I. Preparation of some polyfluoro-1,2-epoxycyclohexanes

Polyfluorocyclohexenes with hydrogen, bromine, and methoxy substituents yielded the corresponding 1,2-epoxides when treated with aqueous sodium hypochlorite containing some acetonitrile. 4,5-Dibromooctafluoro-1,2-epoxycyclohexane was debrominated with zinc dust to give a mixture of octafluoro- and 4H-heptafluoro-1,2-epoxycyolohex- 4-ene. Decafluoro- and 4,5-dibromo-octafluoro-1,2-epoxycyolohexane gave with potassium fluoride in acetonitrile the corresponding potassium perhalogenocyclohexyloxides; heating these gave the analogous cyclohexanones, and treatment with methyl iodide the methyl ethers. The unsaturated 1,2-epoxides also gave methyl ethers on treatment with KF, followed by methylation.