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 |
|---|---|
| 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 |
Cite this
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Aspects of stereochemistry. Part XIX. Directive effects of remote substituents on the alkaline epoxidation of 3-oxo-δ 4 -steroids. / Henbest, H. B.; Jackson, W. R.
In: Journal of the Chemical Society C: Organic Chemistry, 01.12.1967, p. 2459-2465.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Aspects of stereochemistry. Part XIX. Directive effects of remote substituents on the alkaline epoxidation of 3-oxo-δ 4 -steroids
AU - Henbest, H. B.
AU - Jackson, W. R.
PY - 1967/12/1
Y1 - 1967/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0014170866&partnerID=8YFLogxK
U2 - 10.1039/J39670002459
DO - 10.1039/J39670002459
M3 - Article
SP - 2459
EP - 2465
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
SN - 0022-4952
ER -