Aspects of stereochemistry. Part XX. The formation of 5-cyano-3-ketones from 3-oxo-Δ4-steroids

H. B. Henbest, W. R. Jackson

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Reaction of 3-oxo-Δ4-steroids with calcium cyanide in N-methylpyrrolidone gives 5α- and 5β-cyano-3-oxo-steroids. The isomer ratio is close to 1:1 for androstenone, cholestenone and testosterone, and about 3:5 (α:β 5-cyanide) for progesterone.

Original languageEnglish
Pages (from-to)2465-2466
Number of pages2
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
Publication statusPublished - 1 Dec 1967
Externally publishedYes

Cite this

@article{fb2e48a27aac4c3b8c44dd71b8247350,
title = "Aspects of stereochemistry. Part XX. The formation of 5-cyano-3-ketones from 3-oxo-Δ4-steroids",
abstract = "Reaction of 3-oxo-Δ4-steroids with calcium cyanide in N-methylpyrrolidone gives 5α- and 5β-cyano-3-oxo-steroids. The isomer ratio is close to 1:1 for androstenone, cholestenone and testosterone, and about 3:5 (α:β 5-cyanide) for progesterone.",
author = "Henbest, {H. B.} and Jackson, {W. R.}",
year = "1967",
month = "12",
day = "1",
doi = "10.1039/J39670002465",
language = "English",
pages = "2465--2466",
journal = "Journal of the Chemical Society C: Organic Chemistry",
issn = "0022-4952",
publisher = "The Royal Society of Chemistry",

}

Aspects of stereochemistry. Part XX. The formation of 5-cyano-3-ketones from 3-oxo-Δ4-steroids. / Henbest, H. B.; Jackson, W. R.

In: Journal of the Chemical Society C: Organic Chemistry, 01.12.1967, p. 2465-2466.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Aspects of stereochemistry. Part XX. The formation of 5-cyano-3-ketones from 3-oxo-Δ4-steroids

AU - Henbest, H. B.

AU - Jackson, W. R.

PY - 1967/12/1

Y1 - 1967/12/1

N2 - Reaction of 3-oxo-Δ4-steroids with calcium cyanide in N-methylpyrrolidone gives 5α- and 5β-cyano-3-oxo-steroids. The isomer ratio is close to 1:1 for androstenone, cholestenone and testosterone, and about 3:5 (α:β 5-cyanide) for progesterone.

AB - Reaction of 3-oxo-Δ4-steroids with calcium cyanide in N-methylpyrrolidone gives 5α- and 5β-cyano-3-oxo-steroids. The isomer ratio is close to 1:1 for androstenone, cholestenone and testosterone, and about 3:5 (α:β 5-cyanide) for progesterone.

UR - http://www.scopus.com/inward/record.url?scp=37049124375&partnerID=8YFLogxK

U2 - 10.1039/J39670002465

DO - 10.1039/J39670002465

M3 - Article

SP - 2465

EP - 2466

JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

SN - 0022-4952

ER -