The 470 MHz 19F NMR spectra of 1-perfluorohexyl-1-phenylethanol (1a) were measured in toluene-d8. At 0 °C and the lower temperatures, magnetic nonequivalence was observed for the two fluorine nuclei in the CF2 group adjacent to the asymmetric carbon atom and for those in the subsequent four CF2 groups. The extent of the nonequivalence was highly dependent on temperature. 1a and the perfluorooctyl- and perfluorodecyl-homologues were optically resolved and specific rotation of the pure (−)-isomers were examined from the viewpoint of the conformational asymmetry induced on the perfluoroalkyl chain.
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Ute et al. (1992) studied this question.
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