Synlett 2013; 24(8): 1021-1022
DOI: 10.1055/s-0032-1316885
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© Georg Thieme Verlag Stuttgart · New York

β-Oxodithioesters

Girijesh Kumar Verma
Department of Chemistry, Faculty of Science, Banaras Hindu ­University, Varanasi 221005, India   Email: girijesh.vrm@gmail.com
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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.

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Scheme 1 Synthesis of β-oxodithioesters

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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Figure 1 Reactivity profile of β-oxodithioesters