Photocyclization and photooxidation of 3-styrylthiophene
作者:Kai Song、Li-Zhu Wu、Chun-He Yang、Chen-Ho Tung
DOI:10.1016/s0040-4039(00)00097-6
日期:2000.3
The photocyclization, dye-sensitized photooxidation and auto-photooxidation of 3-styrylthiophene have been examined, cis-3-Styrylthiophene undergoes photochemical cis-trans isomerization and cyclization to dihydronaphtho-[1,2-b]thiophene. The quantum efficiency for photocyclization in nonpolar solvents is greater than that in polar solvents. Dye-sensitized photooxidation of 3-styrylthiophene gives benzaldehyde and 3-thiophenecarboxaldehyde. This oxidation proceeds via a superoxide radical anion pathway rather than singlet oxygen pathway. In the presence of oxygen photoirradiation of 3-styrylthiophene solution results in photocyclization, oxidation and dimerization. The mechanism of the latter two reactions was described in terms of formation of a charge transfer complex between oxygen and the substrate. (C) 2000 Elsevier Science Ltd. All rights reserved.
CLARK P. D.; MCKINNON D. M., CAN. J. CHEM., 1981, 59, NO 9, 1297-1302