Acid-promoted cleavage of 4,4-bis(alkylthio)but-3-en-2-one and subsequent thio-Michael addition to α, β-unsaturated ketones

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 alpha,beta-unsaturated ketones 2 affording the corresponding beta-keto sulfides 3 in good yields.