Addition of carbethoxynitrene to trans- and cis-propenylbenzene and the ring-opening of the resulting aziridines

Abstract

Carbethoxynitrene (1) generated thermally from ethyl azidoformate adds stereospecifically to trans- and cis-propenylbenzene. Ring-opening of the aziridines thus produced, proceeds with inversion at the phenyl-substituted carbon in dry acetic acid, while the reaction in aqueous acetic acid occurs with no stereospecificity.