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

Fingerprint

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.
@article{de52ef945f374494aed75c7c37f1c002,
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

UR - http://www.scopus.com/inward/record.url?scp=0035528013&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035528013&partnerID=8YFLogxK

U2 - 10.1023/A:1012737123973

DO - 10.1023/A:1012737123973

M3 - Article

VL - 50

SP - 1419

EP - 1422

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 8

ER -

Access to Document