Reaction of 2,5-dimethylene-2,5-dihydrothiophene with triplet oxygen

Article abstract of DOI:10.1016/S0040-4039(00)73143-1

2,5-Dimethylene-2,5-dihydrothiophene (1), prepared by the pyrolysis of 5-methylthenyl benzoate (3), has been detected by low-temperature NMR spectroscopy. 1 reacts with triplet oxygen to form a cyclic bisperoxide 6. Upon healing 6 decomposes to give 2,5-bis(hydroxymethyl)thiophene (7), 2-formyl-5-hydroxymethylthiophene (8) and 2,5-diformylthiophene (9) in a ratio of 1:2:1, respectively.