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

✍ Scribed by Kai Song; Ming-Li Peng; Ming Xu; Li-Zhu Wu; Li-Ping Zhang; Chen-Ho Tung


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
243 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


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 tetraphenylporphyrin (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.


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