Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane.

J Org Chem

Department of Pathology, Dartmouth Medical School, Hanover, New Hampshire 03755, USA.

Published: September 2002

The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.

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http://dx.doi.org/10.1021/jo0256742DOI Listing

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