[3+2] CYCLOADDITIONS WITH AZIRINE RADICAL CATIONS - A NEW SYNTHESIS OF N-SUBSTITUTED IMIDAZOLES

MULLER F, Mattay J. [3+2] CYCLOADDITIONS WITH AZIRINE RADICAL CATIONS - A NEW SYNTHESIS OF N-SUBSTITUTED IMIDAZOLES. Angewandte Chemie International Edition in English. 1991;30(10):1336-1337.Photoinduced electron-transfer conditions (the photoexcitation of the electron acceptor naphthalenedicarbonitrile (DCN)) are required for [3 + 2] cycloadditions of azirines (1) with imines, which afford N-substituted imidazoles (3). Probable intermediates are the radical cations 2, which were detected by the trapping reaction with trifluoroethanol