Photolysis and photo-oxidation of 3,4-di-tert-butylthiophene 1-oxide

The irradiation of a degassed solution of 3,4-di-tert-butylthiophene 1-oxide in benzene gave 3,4-di-tert-butylthiophene, bis(3,4-di-tert-butyl-2-furyl) disulfide, and 3,4-di-tert-butylfuran in 26%, 15%, and 9% yields, respectively, while the oxidation with singlet oxygen produced 3,4-di-tert-butyl-5-hydroxy-2-furanone, di-tert-butylmaleic anhydride, and 3,4-di-tert-butylthiophene in 59%, 5%, and 2% yields, respectively.