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

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

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 4 , 2007

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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

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Article Details

VOLUME: 4
ISSUE: 4
Year: 2007
Page: [281 - 284]
Pages: 4
DOI: 10.2174/157017807781024318
Price: $65

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