Acylation of cyclic ketones

M. Gorodetsky; E. Levy; R. D. Youssefyeh; Y. Mazur

doi:10.1016/S0040-4020(01)82123-2

Acylation of cyclic ketones

M. Gorodetsky, E. Levy, R. D. Youssefyeh, Y. Mazur

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Abstract

Acylation of steroidal saturated ketones and their enol acetates with acetic anhydride and BF₃-etherate has been studied. α-Acylketones were obtained from 3-keto, 7-keto and 16-keto steroids (I, XII and IX) in the A/B trans series and from 3-ketone (VI) in the A/B cis series. The intermediate difluoroboron chelates (II and VII) were isolated and characterized. No C-acylation of tertiary carbon atom in steroids was observed. The acylation of 2-methylcyclohexanone (XVI) and its enol acetates (XVII and XVIII) is described, and the relation between O-acylation and C-acylation is discussed. Acylation of α,β-unsaturated ketones, testosterone (XXII) and 4-methyltestosterone (XXX) for a comparative short time results in C-6 derivatives (XXIII, XXV and XXXI, and over a longer period of time in difluoroboron chelates (XXVI and XXXIII). The tautomeric equilibrium of the enolic β-diketones IV, XXVII, XXVIII, XXIX and XXXIV is also described.

Original language	English
Pages (from-to)	2039-2051
Number of pages	13
Journal	Tetrahedron
Volume	22
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4020(01)82123-2
State	Published - 1 Jan 1966
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)82123-2

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title = "Acylation of cyclic ketones",

abstract = "Acylation of steroidal saturated ketones and their enol acetates with acetic anhydride and BF3-etherate has been studied. α-Acylketones were obtained from 3-keto, 7-keto and 16-keto steroids (I, XII and IX) in the A/B trans series and from 3-ketone (VI) in the A/B cis series. The intermediate difluoroboron chelates (II and VII) were isolated and characterized. No C-acylation of tertiary carbon atom in steroids was observed. The acylation of 2-methylcyclohexanone (XVI) and its enol acetates (XVII and XVIII) is described, and the relation between O-acylation and C-acylation is discussed. Acylation of α,β-unsaturated ketones, testosterone (XXII) and 4-methyltestosterone (XXX) for a comparative short time results in C-6 derivatives (XXIII, XXV and XXXI, and over a longer period of time in difluoroboron chelates (XXVI and XXXIII). The tautomeric equilibrium of the enolic β-diketones IV, XXVII, XXVIII, XXIX and XXXIV is also described.",

author = "M. Gorodetsky and E. Levy and Youssefyeh, {R. D.} and Y. Mazur",

year = "1966",

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doi = "10.1016/S0040-4020(01)82123-2",

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T1 - Acylation of cyclic ketones

AU - Gorodetsky, M.

AU - Levy, E.

AU - Youssefyeh, R. D.

AU - Mazur, Y.

PY - 1966/1/1

Y1 - 1966/1/1

N2 - Acylation of steroidal saturated ketones and their enol acetates with acetic anhydride and BF3-etherate has been studied. α-Acylketones were obtained from 3-keto, 7-keto and 16-keto steroids (I, XII and IX) in the A/B trans series and from 3-ketone (VI) in the A/B cis series. The intermediate difluoroboron chelates (II and VII) were isolated and characterized. No C-acylation of tertiary carbon atom in steroids was observed. The acylation of 2-methylcyclohexanone (XVI) and its enol acetates (XVII and XVIII) is described, and the relation between O-acylation and C-acylation is discussed. Acylation of α,β-unsaturated ketones, testosterone (XXII) and 4-methyltestosterone (XXX) for a comparative short time results in C-6 derivatives (XXIII, XXV and XXXI, and over a longer period of time in difluoroboron chelates (XXVI and XXXIII). The tautomeric equilibrium of the enolic β-diketones IV, XXVII, XXVIII, XXIX and XXXIV is also described.

AB - Acylation of steroidal saturated ketones and their enol acetates with acetic anhydride and BF3-etherate has been studied. α-Acylketones were obtained from 3-keto, 7-keto and 16-keto steroids (I, XII and IX) in the A/B trans series and from 3-ketone (VI) in the A/B cis series. The intermediate difluoroboron chelates (II and VII) were isolated and characterized. No C-acylation of tertiary carbon atom in steroids was observed. The acylation of 2-methylcyclohexanone (XVI) and its enol acetates (XVII and XVIII) is described, and the relation between O-acylation and C-acylation is discussed. Acylation of α,β-unsaturated ketones, testosterone (XXII) and 4-methyltestosterone (XXX) for a comparative short time results in C-6 derivatives (XXIII, XXV and XXXI, and over a longer period of time in difluoroboron chelates (XXVI and XXXIII). The tautomeric equilibrium of the enolic β-diketones IV, XXVII, XXVIII, XXIX and XXXIV is also described.

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U2 - 10.1016/S0040-4020(01)82123-2

DO - 10.1016/S0040-4020(01)82123-2

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VL - 22

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JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

Acylation of cyclic ketones

Abstract

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