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 language | English |
|---|---|
| Pages (from-to) | 1419-1422 |
| Number of pages | 4 |
| Journal | Russian Chemical Bulletin |
| Volume | 50 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2001 |
Keywords
- Bromination
- Caryophyllene
- Dimethyl sulfoxide
- Hydrobromic acid
- Ketones
- Oxidation
- Tricyclic sesquiterpenoids
ASJC Scopus subject areas
- Chemistry(all)
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Yusubov, M. S., Drygunova, LA., & Tkachev, A. V. (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, 50(8), 1419-1422. https://doi.org/10.1023/A:1012737123973