The suprafacial rearrangement of 3β-hydroxy-5α-hydroperoxy-Δ6-cholestene to the 7α-hydroperoxy-Δ5 isomer does not involve exchange of O2 with the atmosphere, suggesting that it proceeds by a non-dissociative mechanism; on the other hand, the slower subsequent rearrangement of the 7α-Δ5-hydroperoxide to the 7β-Δ5-hydroperoxide is susceptible to exchange, and follows a dissociative mechanism.
A. L. J. Beckwith, A. G. Davies, I. G. E. Davison, A. Maccoll and M. H. Mruzek, J. Chem. Soc., Chem. Commun., 1988, 475 DOI: 10.1039/C39880000475
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