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

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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.

Original languageEnglish
Pages (from-to)2459-2465
Number of pages7
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
Publication statusPublished - 1 Dec 1967
Externally publishedYes

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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journal = "Journal of the Chemical Society C: Organic Chemistry",
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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 journalArticleResearchpeer-review

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AU - Henbest, H. B.

AU - Jackson, W. R.

PY - 1967/12/1

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