Comparative studies on the reactivity of the N-aziridinylimines

Abstract

Comparative studies on the N-aziridinylimines(derived from N-amino-2-phenylaziridine and trans-1-amino-2,3-diphenylaziridine) have been investigated. N-aziridinylimines derived from trans-1-amino-2,3-diphenylaziridine were somewhat more reactive than those from N-amino-2-phenylaziridine. In three types of reactions involving reaction with anions, generation of carbene by thermal decomposition, and $SmI_2$-mediated intramolecular cyclization reactions, N-aziridinylimines derived from trans-1-amino-2,3-diphenylaziridine underwent more facile fragmentation than those from N-amino-2-phenylaziridine. The N-aziridinylimines derived from N-amino-2-phenylaziridine afforded partially fragmented products such as diazo compound 17. On the other hand, the N-aziridinylimines derived from trans-1-amino-2,3-diphenyl aziridine afforded completely fragmented products. These results are due to the fact that E-stilbene has more stable and more steric hindrance than styrene.