Abstract

3-[Bis(ethylthio)methylene]pentane-2,4-dione (1a) and 3-[bis(benzylthio)methylene]pentane-2,4-dione (1b) have been investigated as non-thiolic and odorless thiol equivalents in thia-Michael addition reactions. In the presence of aqueous p-dodecyl benzenesulfonic acid (DBSA), compound (1) was cleaved and the generated thiols underwent facile conjugate addition to α,β-unsaturated ketones 2 in-situ, affording the corresponding β-keto sulfides (3) in good yields.

Keywords: p-Dodecylbenzenesulfonic acid, β-keto sulfides, Michael addition, α,β-unsaturated carbonyl compounds, water