Synthesis and Transformations of 2-(Adamantan-1-yl)aziridine

Abstract

Mono- and disubstituted aziridines derived from sterically hindered olefins of the adamantane series are synthesized. The opening of the aziridine ring under the action of acids is quite a regio- and stereoselective process. Depending on the nature of the nucleophilic agent, the opening of the 2,2-disubstituted aziridine ring can occur by the S_N1 or S_N2 mechanism.