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

H. B. Henbest; W. R. Jackson

doi:10.1039/J39670002465

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

H. B. Henbest, W. R. Jackson

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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 language	English
Pages (from-to)	2465-2466
Number of pages	2
Journal	Journal of the Chemical Society C: Organic Chemistry
DOIs	https://doi.org/10.1039/J39670002465
Publication status	Published - 1 Dec 1967
Externally published	Yes

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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",

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doi = "10.1039/J39670002465",

language = "English",

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

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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.

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U2 - 10.1039/J39670002465

DO - 10.1039/J39670002465

M3 - Article

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AN - SCOPUS:37049124375

SN - 0022-4952

SP - 2465

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JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

ER -

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

Abstract

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