Thia-Michael Addition Reactions in Water Using 3-[Bis(Alkylthio) Methylene] Pentane-2,4-Diones as Odorless and Efficient Thiol Equivalents

Title: Thia-Michael Addition Reactions in Water Using 3-[Bis(Alkylthio) Methylene] Pentane-2,4-Diones as Odorless and Efficient Thiol Equivalents

Volume: 4 Issue: 4

Author(s): Yanyan Chai, Dewen Dong, Yan Ouyang, Yongjiu Liang, Yan Wang, Minghui Li and Qun Liu

Affiliation:

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

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.

Cite this article as:

Yanyan Chai , Dewen Dong , Yan Ouyang , Yongjiu Liang , Yan Wang , Minghui Li and Qun Liu , Thia-Michael Addition Reactions in Water Using 3-[Bis(Alkylthio) Methylene] Pentane-2,4-Diones as Odorless and Efficient Thiol Equivalents, Letters in Organic Chemistry 2007; 4 (4) . https://dx.doi.org/10.2174/157017807781024318