Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 17, Pages 12853-12856Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01369
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A mild and less hazardous method for converting 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation and reduction is presented.
2-(Methylthio)-1,3-dithioles are important heterocyclic compounds used for the preparation of redox-active derivatives of tetrathiafulvalene as they serve as precursors for phosphonate esters that can be employed in Horner-Wadsworth Emmons olefination reactions. Here, we present a mild and less hazardous method than previous methods for converting readily accessible 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation with trimethyl orthoformate and HBF4.Et2O and a subsequent reduction with NaBH4.
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