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Reactions with Azirridines, 36 Arene Hydrides 2 SN2 and SET Reactions of N-Acylaziridines with Diphenylmethanide and "Naphthalene Hydride" (Anion of Dihydronaphthalene)
Woderer, Anton,Stamm, Helmut
, p. 2050 - 2054 (2007/10/02)
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 50percent.The formation of by-products from 6b and 6c can be rationalized 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.
