Novel [2 + 2] photocycloaddition-induced rearrangement of bichromophoric naphthalene-tethered resorcinol ethers.
The first examples of sequential photocycloaddition-rearrangement reactions of naphthalene-tethered resorcinol ethers are described. Bichromophoric aromatic compounds with naphthalene and resorcinol ether moieties were irradiated in the presence/absence of a small amount of acid to give the corresponding cycloaddition-rearrangement products. From the determination of quantum yields, steady-state fluorescence spectral studies, and fluorescence lifetime measurements, the mechanism of this novel photoinduced multistep reaction was elucidated to involve the initial intramolecular exciplex formation, followed by the intramolecular [2 + 2] photocycloaddition between the two aromatic rings and the subsequent acid-catalyzed skeletal rearrangement of the resulting cyclobutane derivative leading to the final products.
Hoffmann
Norbert
N
Laboratoire des Réactions Selectives et Applications, UMR CNRS et Université de Reims Champagne-Ardenne, France. norbert.hoffman@univ-reims.fr
Pete
Jean-Pierre
JP
Inoue
Yoshihisa
Y
Mori
Tadashi
T