Role of the electron-donating methoxy group on the photo-induced cyclization of 2-azadienes: A mechanistic study

  1. Campos, P.J. 1
  2. Caro, M. 1
  3. Rodríguez, M.A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Año de publicación: 2013

Volumen: 69

Número: 37

Páginas: 7950-7955

Tipo: Artículo

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DOI: 10.1016/J.TET.2013.07.015 SCOPUS: 2-s2.0-84880918189 WoS: WOS:000323140100008 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

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Resumen

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.