Photoreactions of cisoid 1,4-diphenyl-1,3-butadienes. Direct irradiation in solution and in low temperature organic glass

Autor: Krishnamoorthy, G., Schieffer, Stefan, Pescatore, John, Ulsh, Richard, Liu, Robert S. H., Liu, Jin
Zdroj: Photochemical & Photobiological Sciences; November 2004, Vol. 3 p1047-1051, 5p
Abstrakt: The photoreactions of 1,4-diphenyl-1,3-butadienes (DPB) fused with a bicyclo[2.2.1]heptano ring under direct irradiation were examined in solution at room temperature and in organic glass at liquid nitrogen temperature. Photocyclization yielding a phenylnaphthalene compound was shown to be preceded by facile E,Eto E,Zphotoisomerization. The reverse E,Zto E,Eisomerization took place with equal ease in low temperature organic glass and in solution at room temperature. The pattern of reaction at low temperature is consistent with the involvement of the Hula-twist mechanism. However, complexity in conformational population, suggested by ab initiocalculated data, made the experimental evidence less clear-cut than in previously reported examples of HT.
Databáze: Supplemental Index