In the absence of a nucleophile, the thiete dioxide product formed through elimination was isolated in high yield (Scheme 2a). Thiete dioxides have themselves have been demonstrated as suitable substrates for further reactions including cycloaddition, metalation and C-H functionalization. 15 The effect of phenolic nucleophiles on elimination were investigated in a competition experiment. Both resorcinol and dimethoxybenzene undergo Friedel-Crafts alkylation with thietanol 2a in high yield, but 4a is formed only with resorcinol. A competition experiment with a 1:1 mixture of resorcinol and dimethoxybenzene gave only the phenolic product,3ak, but also formed thietene 4a, suggestive of a non-innocent role of the phenolic hydroxyl groups in the elimination process (Scheme 2a). Treating 2a with the resorcinol alone does not result in elimination, suggesting a role as a basic site, perhaps via an O-linked intermediate. 9b