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
AN - SCOPUS:0035528013
VL - 50
SP - 1419
EP - 1422
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 1066-5285
IS - 8
ER -