4.4 Article

Thionation of esters and lactones with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane

Journal

TETRAHEDRON LETTERS
Volume 43, Issue 3, Pages 371-373

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)02144-X

Keywords

thioesters; thiocarbonyl compounds; thiophosphates; silicon and compounds

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The combination of P4S10 and hexamethyldisiloxane converts esters and lactones to thionoesters and thionolactones in yields 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. (C) 2002 Elsevier Science Ltd. All rights reserved.

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