Novel [2 + 2] photocycloaddition-induced rearrangement of bichromophoric naphthalene-tethered resorcinol ethers |
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Authors: | Hoffmann Norbert Pete Jean-Pierre Inoue Yoshihisa Mori Tadashi |
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Affiliation: | Laboratoire des Réactions Selectives et Applications, UMR CNRS et Université de Reims Champagne-Ardenne, France. norbert.hoffman@univ-reims.fr |
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Abstract: | 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. |
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