On the other hand, treating 4a with resorcinol under the catalytic conditions formed 3ak in a high 88% yield. Together, this suggests a more complex role for the phenol nucleophiles to both promote the elimination pathway but also return the thiete dioxide to the catalytic cyclic through protonation. The chemical stability of 3,3-disubstituted thietane-1,1-dioxides was investigated by submitting thietan-3-ol 2a, diarylthietane dioxide 3aa, and sulfide 5ab to a range of conditions (Scheme 2b). In general, quantitative recovery of the substrates was observed across acidic (1 M HCl at 37 ºC) and basic conditions (1 M NaOH), as well as in the presence of nucleophiles (NaI, and cysteine methyl ester). On treatment with aqueous 1 M NaOH, thietan-3-ol dioxide 2a degraded via elimination to thietene 4a.