40669-41-8Relevant articles and documents
Base-Catalyzed Transesterification of Thionoesters
Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
, p. 12784 - 12792 (2018/10/20)
Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
Compositions and methods for thionation during chemical synthesis reactions
-
, (2008/06/13)
Compositions and methods for using these compositions to produce high yields of thionated compounds are provided.
Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J.
, p. 6461 - 6473 (2007/10/03)
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.
