The photochemistry of thiophene S-oxides

Thiophene S-oxides have been prepared and their photoreactivity has been studied. In many cases, the sulfur moiety of the thiophene S-oxides is deoxygenated. Here, the corresponding thiophenes or hydroxylated thiophenes are isolated. In the case of the photoirradiation of tert-butyl substituted thiophene S-oxides, the oxygen of the sulfoxy unit is incorporated into the heterocyclic ring system and the corresponding furans have been isolated. Also, structures with two thiophene cores have been oxidized to the respective thiophene S-oxides. These molecules undergo photodeoxygenation, a reaction, which is catalysed by (non-oxidized) thiophenes.