Aspects of stereochemistry. Part XIX. Directive effects of remote substituents on the alkaline epoxidation of 3-oxo-δ
                        4
                        -steroids

H. B. Henbest; W. R. Jackson

doi:10.1039/J39670002459

Aspects of stereochemistry. Part XIX. Directive effects of remote substituents on the alkaline epoxidation of 3-oxo-δ ⁴ -steroids

H. B. Henbest, W. R. Jackson

Research output: Contribution to journal › Article › Research › peer-review

50 Citations (Scopus)

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	https://doi.org/10.1039/J39670002459
Publication status	Published - 1 Dec 1967
Externally published	Yes

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10.1039/J39670002459

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Cite this

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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. ",

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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

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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.

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