Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2: H -azirines via an SN2′-SN2′ cascade in 2-halo-2 H -azirines

Abstract

Various 2-oxygen-substituted 2H-azirine-2-carboxylic acid derivatives were synthesized in high yields under mild conditions from readily available precursors, 2-halo-2H-azirines and OH-reagents having pKa values in the range of 3-10. This reaction is the first example of substitution at the azirine carbon atom for which an unusual SN2′-SN2′ cascade mechanism was revealed.