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

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

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 8 , 2005

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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.

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

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Article Details

VOLUME: 2
ISSUE: 8
Year: 2005
Page: [755 - 759]
Pages: 5
DOI: 10.2174/157017805774717535
Price: $65

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