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- Title
Oxidation of Cage Derivatives of Quinopimaric Acid.
- Authors
Vafina, G. F.; Lobov, A. N.
- Abstract
The oxidation of cage compounds derived from quinopimaric acid, namely γ-diketone, oxa-"bird cage," 18-chloro-15-oxa-"bird cage," and 16-sulfanyl-15-oxa-"bird cage," was studied using a number of oxidating agents, including sodium percarbonate in trifluoroacetic acid at 0°C, 36% hydrogen peroxide in acetone at room temperature, and tert-butyl hydroperoxide in the presence of MoCl5 in boiling benzene. It was shown for the first time that the oxidation of diterpene oxa-"bird cages" led to the formation of mixtures of keto lactones (Baeyer–Villiger oxidation products), in which 7,10-dioxo-6-oxaheptacyclo[11.8.0.03,8.04,12.05,11.09,13.016,21]heneicosane was the major component.
- Subjects
BIRDCAGES; BAEYER-Villiger rearrangement; ACID derivatives; HYDROPEROXIDES; OXIDATION; TRIFLUOROACETIC acid
- Publication
Russian Journal of Organic Chemistry, 2024, Vol 60, Issue 3, p423
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428024030084