Reactive intermediates. Part X. Synthesis of aziridines from aminonitrenes and olefins

Abstract

Oxidation of N-aminophthalimide, 3-amino-2-methyl-4-quinazolone, and 1-amino-2-quinolone with lead tetra-acetate in the presence of a wide range of electrophilic and nucleophilic olefins is a useful, stereospecific route to aziridines. The generation and cycloaddition of singlet amino-nitrenes is proposed.

Several chloro- and bromo-substituted aziridines undergo an almost quantitative, uncatalysed thermal rearrangement, with opening of the aziridine ring, to give hydrazones.