A, comparative study on photosensitized oxidation of trans-2-vinylthiophenes with trans-3-vinylthiophenes

作者：Song, K; Peng, ML; Xu, M; Wu, LZ; Zhang, LP; Tung, CH^*

来源：Tetrahedron Letters, 2002, 43(37): 6633-6636.

DOI：10.1016/S0040-4039(02)01445-4

• SINGLET OXYGEN
• ELECTRON

The photosensitized oxidation of trans-2-styrylthiophenes (trans-2-ST). trans-3-styrylthiophenes (trans-3-ST) and trans-1,2-di(2-thienyl)ethylene (trans-2-TE) were investigated using the sensitizers tetraplenylporphyrin (TPP) in a non-polar solvent and 9, 10-dicyanoanthracene (DCA) in a polar solvent. The oxidation pathway is dependent on the position of the vinyl substituent in the thiophene ring. While trans-2-ST and trans-2-TE only undergo photooxidation via the singlet oxygen pathway to yield [4+2] and [2+2] products, the photosensitized oxidation of trans-3-ST proceeds exclusively via the superoxide anion pathway to produce the thiophenecarboxaldehyde and benzaldehydes. All of the above substrates May undergo auto-photooxidation via a charge-transfer complex of the substrate and oxygen.

• 出版日期2002-9-9
• 单位中国科学院理化技术研究所