417707-61-0Relevant academic research and scientific papers
Novel [2 + 2] photocycloaddition-induced rearrangement of bichromophoric naphthalene-tethered resorcinol ethers
Hoffmann, Norbert,Pete, Jean-Pierre,Inoue, Yoshihisa,Mori, Tadashi
, p. 2315 - 2322 (2007/10/03)
The first examples of sequential photocycloaddition-rearrangement reactions of naphthalenetethered 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.
New photochemical rearrangements and extrusion reactions of aromatic compounds induced by an intramolecular [2+2] photocycloaddition between a naphthalene and a resorcinol moiety
Hoffmann, Norbert
, p. 7933 - 7941 (2007/10/03)
An intramolecular [2+2] photocycloaddition between a naphthalene and a resorcinyl moiety was followed by an acid catalyzed rearrangement leading to tricyclic tetrahydrofuran derivatives. The reaction was efficient when the irradiation was carried out at 300nm. For the first time, an extrusion of a RCOCH3 (R=H or alkyl) fragment from the tetrahydrofuran ring was observed when the tricyclic tetrahydrofuran derivatives were irradiated at 254nm. Reaction rate and yield depended on the substitution pattern. In particular, significantly different quantum yields were measured in the case of different diastereoisomers.
