Synthesis of triterpenoid-based 1,2,4-trioxolanes and 1,2,4-dioxazolidines by ozonolysis of allobetulin derivatives
✍ Scribed by Oxana B. Kazakova; Dmitri V. Kazakov; Emil Yu. Yamansarov; Natal’ya I. Medvedeva; Genrikh A. Tolstikov; Kyrill Yu. Suponitsky; Dmitri E. Arkhipov
- Publisher
- Elsevier Science
- Year
- 2011
- Tongue
- French
- Weight
- 362 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4039
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Electron-transfer photooxygenation of l-butyl-2,3\_diphenylaziridine with 9,10dicyanoanthracene in oxygen-saturated acetonitrile yields 4-butyl-3,5-diphenyl-1,2,4dioxazolidine. This peroxide is surprisingly stable in nonpolar solvents decomposing to benzaldehyde and N-butylbenzamide upon heating to
distillation under high vacuum at room temperature (time required ca. 48 h). Double recrystallization of the residue from pentane afforded (2) in 50 to 55% yield (based on ( I ) ) . For conversion of (2) into (3) a solution of (2) (2.3 mmol) and Fe(CO), (3 ml) in ether (50 ml) was irradiated at -40