Reaktionen mit Aziridinen, 36. Arenhydride, 2. S N 2‐ und SET‐Reaktionen von N ‐Acylaziridinen mit Diphenylmethanid und „Naphthalinhydrid”︁ (Anion von Dihydronaphthalin)

Reactions with Aziridines, 36 Arene Hydrides 2. S N 2 and SET Reactions of N ‐Acylaziridines with Diphenylmethanide and „Naphthalene Hydride” (Anion of Dihydronaphthalene) Diphenylmethane is incompletely deprotonated by sodium naphthalenide in THF so that some „naphthalene hydride” 4 (anion of 1,4‐dihydronaphthalene) remains present in the deprotonation equilibrium. The generated diphenylmethanide anion 3a reacts with the N ‐acylaziridines 6a–c to form the expected amidoethyl derivatives 7a–c in yields of less than 50%. The formation of by‐products from 6b and 6c can be rationlized on the basis of classic ionic mechanisms. However, for 6a the by‐product N ‐ethylbenzamide clearly points to a SET mechanism with „naphthalene hydride” 4 as the electron source and with the radical 8 as a hydrogen source.