In epoxidation of the conformationally biassed 5-t-butylcyclohex-2-enols by peroxybenzoic acid, higher cis-stereoselectivity and faster rate are found for the pseudo-equatorial than for the pseudo-axial alcohol. Cyclo-oct-2-en-1-ol is epoxidised with stereospecific introduction of the epoxy-group trans to hydroxy, and appropriate acyclic allylic alcohols show a preference for formation of the threo-epoxy-alcohol. A consistent interpretation of these results is advanced, based on the postulate that the preferred conformation of an allylic alcohol in the transition state for epoxidation is as in (XX).
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Chamberlain et al. (1970) studied this question.