Abstract
3-Oxo-Δ 4 -steroids that do not contain polar substituents react with alkaline hydrogen peroxide to give 3-oxo-4β,5β-epoxides. Up to 30% of the α-epoxy-ketone is formed when the steroid contains a polar group at C-17 or beyond; this result is discussed in terms of electrostatic interactions between the polar substituent and the anionic transition states. Polar substituents at C-11 show stronger directive effects.
Original language | English |
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Pages (from-to) | 2459-2465 |
Number of pages | 7 |
Journal | Journal of the Chemical Society C: Organic Chemistry |
DOIs | |
Publication status | Published - 1 Dec 1967 |
Externally published | Yes |