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Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. AstraZeneca R&D, Pharmaceut Dev, Sweden.
2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 6, 1546-1553 p.Article in journal (Refereed) Published
Abstract [en]

Tetraphosphorus decasulfide (P 4S 10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (̃165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P 4S 10 in pyridine or LR, have been removed.

Place, publisher, year, edition, pages
2011. Vol. 76, no 6, 1546-1553 p.
Keyword [en]
Acridones, Crystalline form, Dimethyl sulfone, Glycyl-glycine, High temperature, Lawesson reagent, Rapid decomposition, Acetonitrile, Crystalline materials, Pyridine, X ray crystallography, Organic solvents, acridone derivative, glycylglycine, indole, phosphorus, piperazine derivative, pyridine derivative, reagent, solvent, sulfone, sulfur, tetraphosphorus decasulfide, unclassified drug, article, chemical structure, complex formation, crystal structure, decomposition, Acetonitriles, Amides, Dimethyl Sulfoxide, Models, Molecular, Molecular Conformation, Pyridines, Solvents, Sulfones
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-151233DOI: 10.1021/jo101865yISI: 000288142800004Scopus ID: 2-s2.0-79953906150OAI: oai:DiVA.org:kth-151233DiVA: diva2:747609
Note

QC 20140917

Available from: 2014-09-17 Created: 2014-09-15 Last updated: 2017-12-05Bibliographically approved

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