Cycloreversion of azetidines via oxidative electron transfer. steady-state and time-resolved studies |
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Authors: | Andreu Inmaculada Delgado Julio Espinós Amparo Pérez-Ruiz Raul Jiménez M Consuelo Miranda Miguel A |
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Institution: | Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Valencia, Spain. |
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Abstract: | Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c-2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5 (*+)). Stepwise C-N and C-C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as final products. Mechanistic evidence is provided by quenching studies, using laser flash photolysis to generate 5 (*+) from its neutral precursor. |
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