Highly electronegative substituents at either C-3 or C-17 in steroidal 5,6-epoxides suppress C-5 carbonium ion rearrangements in favour of fluorohydrin formation. The 6α,9α-epoxy-1 (10 → 5)abeo-cholestane structures (37) and (38) are assigned to previously isolated compounds.
I. G. Guest and B. A. Marples, J. Chem. Soc., Perkin Trans. 1, 1973, 900 DOI: 10.1039/P19730000900
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