Dynamic Thiol Exchange with β-Sulfido-α,β-Unsaturated Carbonyl Compounds and Dithianes

A reversible covalent bond exchange of thiols, beta-sulfido-alpha,beta-unsaturated carbonyls, and dithianes has been studied in DMSO and D2P/DMSO mixtures. The equilibrium between thiols and beta-sulfido-alpha,beta-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the beta-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry.