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DOI: 10.1055/s-0032-1316885
β-Oxodithioesters
Publication History
Publication Date:
16 April 2013 (online)
Introduction
β-Oxodithioesters 1, sulfur analogues of β-ketoesters, are important synthons frequently used for the synthesis of heterocycles. 1 can easily be synthesized by the reaction of methyl ketones (or active methylene compounds) with dialkyl-, allyl-, or benzyl trithiocarbonates in the presence of NaH (Scheme [1]).[1] These versatile reagents are yellow and have a low melting point as well as an offensive odor.
Other synthons such as β-oxothioamides and S,S- or N,S-acetals can also be synthesized from 1.[2] [3] Figure [1] shows the reactivity profile of β-oxodithioesters: the carbon atoms of the carbonyl and thiocarbonyl groups are electrophilic centers while oxygen, sulfur, and the carbon of the active methylene group are nucleophilic centers.
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References
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