Réarrangement thermique comparé de vinylaziridines <i>cis</i> et <i>trans</i>

Abstract

The stereospecific syntheses of the cis- and trans-diethylenic aziridines 3a–d and phenylvinylaziridines 3e–g was achieved with the corresponding epoxides 1a–g as starting materials.cis-Divinylaziridine, 3a, is not stable at ordinary temperatures; the Cope rearrangement of cis-dipropenylaziridine, 3c, yields cis-dihydroazepine, 4c. Thermolysis of the trans-divinylaziridines 3a–d leads to the dihydroazepines while that of the phenylvinylaziridines yields 2-pyrrolines. The results are compared with those obtained in the epoxide series. [Journal translation]