Abstract
Singlet oxygen reacts with 2,5-dimethylthiophene (1) exclusively by (4+2)-cycloaddition to yield the thiaozonide 2. The structure of this product is inferred from its 1H- and 13C NMR spectra. Neat thiaozonide 2 decomposes violently at room temperature. In aprotic non-polar and in protic polar solvents it is slowly transformed into cis-sulfine 3c and cis-2,5-dione 4c, which rearranges to the trans-isomer 4t. A mechanism for the transformation reaction is proposed.
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