Non-sensitized photooxygenation of some steroidal isoxazolidines

✍ Scribed by Ljubinka B. Lorenc; Ivan O. Juranić; Milan M. Dabović; Mihailo Lj. Mihailović

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 627 KB
• Volume: 47
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86567-4

✦ Synopsis

W irradiation of the steroidal tsoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular o_aygen. re.wlts in oxidative cleavage of the epoxyimino bridge to give sew& products; the N--unsubstituted isoxazolidine 2x1 horded the nitro products 3,4, and 5 and the azoq ampounds 6 and 7, whik the N-methyl and N-acetyl akrivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole ident@abk material. An explanation of the observed photooqgenation processe-v involving acipkx formation followed by

proton transfw from isoxazolidine to mokcular oxygen is presented.