Acid-Promoted Cleavage of 4,4-Bis(Alkylthio)But-3-en-2-One and Subsequent Thio-Michael Addition to α,β-Unsaturated Ketones

Title: Acid-Promoted Cleavage of 4,4-Bis(Alkylthio)But-3-en-2-One and Subsequent Thio-Michael Addition to α,β-Unsaturated Ketones

Volume: 2 Issue: 8

Author(s): Haifeng Yu, Dewen Dong, Yan Ouyang, Qun Liu and Yan Wang

Affiliation:

Keywords: 4,4-Bis(alkylthio)but-3-en-2-one, thiol equivalent, thio-Michael addition, α,β-unsaturated ketone

Abstract: 4,4-Bis(ethylthio)but-3-en-2-one 1a and 4,4-bis(benzylthio)but-3-en-2- one 1b have been investigated as non-thiolic and odorless thiol equivalents in thio-Michael addition. Promoted by acetyl chloride in methanol, the cleavage of compounds 1a and 1b commenced and the in-situ generated thiols underwent facile acid-catalyzed conjugate addition to α,β-unsaturated ketones 2 affording the corresponding β-keto sulfides 3 in good yields.

Cite this article as:

Yu Haifeng, Dong Dewen, Ouyang Yan, Liu Qun and Wang Yan, Acid-Promoted Cleavage of 4,4-Bis(Alkylthio)But-3-en-2-One and Subsequent Thio-Michael Addition to α,β-Unsaturated Ketones, Letters in Organic Chemistry 2005; 2 (8) . https://dx.doi.org/10.2174/157017805774717535