Rotational isomerism in epifluorohydrin

Abstract

The complete analysis of the ¹H and ¹⁹F n.m.r. spectra of epifluorohydrin in four different solvents is reported. The parameters obtained are used to predict the predominant rotational isomers of the molecule. The long-range coupling constants to fluorine are opposite in sign, in accordance with recent results, and the long-range proton–proton coupling constants are small or negligible. A large chemical shift difference between the protons of the CH₂F group is explained on the grounds of the proposed rotational isomers, and the anisotropic effect of the epoxide ring.