Acylation of cyclic ketones

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

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


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 languageEnglish
Pages (from-to)2039-2051
Number of pages13
Issue number7
StatePublished - 1 Jan 1966
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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