Abstract
A convenient and efficient protocol for the thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutan-amides as thiol equivalents has been developed. Promoted by sodium hydroxide (NaOH) in ethanol at room temperature, the cleavage commences and the generated thiolate anions undergo nucleophilic addition in situ. β-Hydroxy sulfides were obtained in high yields along with good (3-regioselectivity, and trans β-hydroxy sulfides were also isolated. The thiolysis of one α,β-epoxyketone product with the thiol equivalents was accomplished to afford the corresponding α-carbonyl sulfides in excellent yields. In all the cases, 3-oxo-N-o-tolylbutanamide, the precursor of the thiol equivalents, could be recovered in the novel thiolysis process as a byproduct in good yield.
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