Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane.
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.
Department of Pathology, Dartmouth Medical School, Hanover, New Hampshire 03755, USA. tjc@nimbus.dartmouth.edu
Thomas J
TJ
Curphey
D000577:Amides / Q000737:chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D009946:Organothiophosphorus Compounds / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry; D012833:Siloxanes / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D000577:Amides; D004952:Esters; D007659:Ketones; D007769:Lactams; D007783:Lactones; D009943:Organophosphorus Compounds; D009946:Organothiophosphorus Compounds; D012833:Siloxanes; D013440:Sulfides; D013455:Sulfur