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

53 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

Access to Document

10.1039/J39670002459

Cite this

@article{13292e98c1164139b63762657272b78b,

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

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. ",

author = "Henbest, {H. B.} and Jackson, {W. R.}",

year = "1967",

month = dec,

day = "1",

doi = "10.1039/J39670002459",

language = "English",

pages = "2459--2465",

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

issn = "0022-4952",

publisher = "The Royal Society of Chemistry",

}

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

C2 - 6070202

AN - SCOPUS:0014170866

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 -

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

Abstract

Access to Document

Other files and links

Cite this

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