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[3 + 2] Cycloadditions with Azirine Radical Cations: A New Synthesis of N ‐Substituted Imidazoles
Author(s) -
Müller Felix,
Mattay Jochen
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199113361
Subject(s) - photoexcitation , azirine , chemistry , photochemistry , electron transfer , electron acceptor , photoinduced electron transfer , radical ion , medicinal chemistry , organic chemistry , ion , excited state , ring (chemistry) , physics , nuclear physics
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.