Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown
Published: June 5, 2025
We describe the synthesis of a series readily assembled, variously substituted 3-(4-trifluoromethyl-2-nitrobenzenesulfonamido)alkyl silylperoxides and their conversion to corresponding isoxazolidines in moderate high yield by intramolecular N-O bond formation on removal sulfonamide protecting group. Cyclization with was dependent steric hindrance electrophilic silylperoxides, primary systems cyclizing directly during course cleavage thiolate anions. Secondary silyl peroxides, other hand, were best cyclized warming presence hexafluoroisopropanol after desulfonylation, while tertiary required deprotonation intermediate amine. Tertiary benzylic peroxides underwent cyclization novel mechanism, trifluoromethylnitrophenyl fluoride-mediated desilylation. The extended include simple oxazine, but extrapolation an oxazepine foiled competing Kornblum DeLaMare fragmentation at level aminoperoxide.
Language: Английский