Role of the electron-donating methoxy group on the photo-induced cyclization of 2-azadienes: A mechanistic study
- Campos, P.J. 1
- Caro, M. 1
- Rodríguez, M.A. 1
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1
Universidad de La Rioja
info
ISSN: 0040-4020
Any de publicació: 2013
Volum: 69
Número: 37
Pàgines: 7950-7955
Tipus: Article
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Resum
A combined experimental and computational investigation has shown that the photocyclization of 2-azadienes to isoquinolines is consistent with a unimolecular process in the triplet state and that the (n,π*) transition is involved. The presence of a methoxy group favours the photoreaction. According to calculations, the reaction should proceed by a conformational equilibrium in the ground state followed by excitation and subsequent cyclization. The presence of an equilibrated triplet-state intermediate along the reaction path is consistent with a measurable luminescence. © 2013 Elsevier Ltd. All rights reserved.