Abstract
A series of 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOHin EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α,β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-N-o-tolylbutanamide 4, the precursor of compounds 1, can be recovered from the novel thia-Michael addition reactions as a byproduct in good yield.
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