Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system

M. S. Yusubov, Larisa Alexandrovna Drygunova, A. V. Tkachev

Research output: Contribution to journal › Article

1 Citation (Scopus)

Abstract

Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded α,β-unsaturated a-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated, which provide evidence that oxidation proceeds according to the following scheme: ketone→α-bromoketone→α,α-dibromoketone→α, β-unsaturated α-bromoketone.

Original languageEnglish
Pages (from-to)1419-1422
Number of pages4
JournalRussian Chemical Bulletin
Volume50
Issue number8
DOIs
Publication statusPublished - 2001

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Dimethyl Sulfoxide
Ketones
Oxidation
Aromatization
Derivatives

Keywords

  • Bromination
  • Caryophyllene
  • Dimethyl sulfoxide
  • Hydrobromic acid
  • Ketones
  • Oxidation
  • Tricyclic sesquiterpenoids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system. / Yusubov, M. S.; Drygunova, Larisa Alexandrovna; Tkachev, A. V.

In: Russian Chemical Bulletin, Vol. 50, No. 8, 2001, p. 1419-1422.

Research output: Contribution to journal › Article

Yusubov, MS, Drygunova, LA & Tkachev, AV 2001, 'Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system', Russian Chemical Bulletin, vol. 50, no. 8, pp. 1419-1422. https://doi.org/10.1023/A:1012737123973
Yusubov MS, Drygunova LA, Tkachev AV. Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system. Russian Chemical Bulletin. 2001;50(8):1419-1422. https://doi.org/10.1023/A:1012737123973
Yusubov, M. S. ; Drygunova, Larisa Alexandrovna ; Tkachev, A. V. / Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system. In: Russian Chemical Bulletin. 2001 ; Vol. 50, No. 8. pp. 1419-1422.
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AU - Drygunova, Larisa Alexandrovna

AU - Tkachev, A. V.

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AB - Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded α,β-unsaturated a-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated, which provide evidence that oxidation proceeds according to the following scheme: ketone→α-bromoketone→α,α-dibromoketone→α, β-unsaturated α-bromoketone.

KW - Bromination

KW - Caryophyllene

KW - Dimethyl sulfoxide

KW - Hydrobromic acid

KW - Ketones

KW - Oxidation

KW - Tricyclic sesquiterpenoids

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