1 serves as a model compound for natural products in which an OH-group is attached to an asymmetric C-atom. It was oxidized with PbO2 to the paramagnetic phenoxy radical 2. After addition of a chiral amine, two signals appeared in the ENDOR spectrum in the ratio 1:1 for the H-atom at the asymmetric C-atom. They are assigned to the two enantiomers (R)-2 and (S)-2.
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Stegmann et al. (1986) studied this question.
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