

STRUCTURAL TRANSFORMATIONS OF 2-(ADAMANTAN-1-YL)AZIRIDINES

Abstract
The specifics of transformations of sterically hindered 2-(adamantan-1-yl)aziridine derivatives in the presence of trifluoroacetic anhydride are considered. In a reaction with trifluoroacetic anhydride, trans-2-(adamantan-1-yl)-3-methylaziridine forms the rearrangement product dihydro-1,3-oxazine condensed with homoadamantane, whereas 2-(adamantan-1-yl)aziridine forms a mixture of a derivative of oxazine and N-[1-(adamantan-1-yl)-2-hydroxyethyl]-2,2,2-trifluoroacetamide in equal proportions.
Keywords
adamantane; aziridine; dihydro-1,3-oxazines; cage compounds; ring opening reactions; skeletal rearrangements.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv