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 journalArticle

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

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title = "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",
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.",
keywords = "Bromination, Caryophyllene, Dimethyl sulfoxide, Hydrobromic acid, Ketones, Oxidation, Tricyclic sesquiterpenoids",
author = "Yusubov, {M. S.} and Larisa Alexandrovna Drygunova and Tkachev, {A. V.}",
year = "2001",
doi = "10.1023/A:1012737123973",
language = "English",
volume = "50",
pages = "1419--1422",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer New York",
number = "8",

}

TY - JOUR

T1 - 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

AU - Yusubov, M. S.

AU - Drygunova, Larisa Alexandrovna

AU - Tkachev, A. V.

PY - 2001

Y1 - 2001

N2 - 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.

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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U2 - 10.1023/A:1012737123973

DO - 10.1023/A:1012737123973

M3 - Article

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SP - 1419

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JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

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