The trimethylamine hydrofluoride [(CH3)3N, 2HF] action on epoxyalcohols 2c, 2d and epoxyacetate 2e derived from bicyclo [3.1.1.] heptane does not give exclusively substitued fluorocyclohexenes. The action of the same reagent on epoxyalcohols 4c, 4d and epoxyacetate 4e derived from cyclohexane leads to fluoride derivatives. Epoxycarbonyl compounds 2a, 4a and 2b do not give any reaction under the same conditions excepting the epoxyketone 4b which leads to fluoroalcoholketones 4'b and 4"b.
M.M. El Gaied, A. Selmi