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...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-09, Vol.67 (18), p.6461-6473
Main Author: Curphey, Thomas J
Format: Article
Language:English
Subjects:
Aliphatic compounds
Amides - chemistry
Chemistry
Chromatography, Gas
Chromatography, High Pressure Liquid
Combinatorial Chemistry Techniques
Esters - chemistry
Exact sciences and technology
Ketones - chemistry
Lactams - chemistry
Lactones - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Organic chemistry
Organophosphorus Compounds - chemistry
Organothiophosphorus Compounds - analysis
Organothiophosphorus Compounds - chemical synthesis
Organothiophosphorus Compounds - chemistry
Preparations and properties
Siloxanes - chemistry
Sulfides - chemistry
Sulfur - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0256742