The Reaction of Cyanothioformamide with Isocyanates − Formation of a Disulfide by Reduction of a Thiocarbonyl Group

Autor:	G. Adiwidjaja, Roger Ketcham, Ernst Schaumann
Rok vydání:	2001
Předmět:	Ethanol Aryl Organic Chemistry chemistry.chemical_element Methyl isocyanate Redox Medicinal chemistry Sulfur Flue-gas desulfurization chemistry.chemical_compound chemistry Group (periodic table) Organic chemistry Physical and Theoretical Chemistry Imidazolidines
Zdroj:	European Journal of Organic Chemistry. 2001:1695-1699
ISSN:	1099-0690 1434-193X
DOI:	10.1002/1099-0690(200105)2001:9<1695::aid-ejoc1695>3.0.co;2-0
Popis:	The reactions of the title compounds are governed by sulfur redox chemistry. Thus, cyanothioformamide 2 reacts with aryl isocyanates 3a−c to give bis[3-aryl-1-(arylcarbamoyl)-2-oxo-4-(arylcarbamoylimino)imidazolidin-5-yl] disulfides 6, as shown by an X-ray crystallographic investigation of product 6a. Reaction with methyl isocyanate (3d) gives the related trisulfide 7d along with disulfide 6d. A desulfurized product, imidazolinone 10, could also be isolated from the methyl isocyanate reaction and was characterized by X-ray diffraction analysis. In boiling ethanol, 6a and 7d undergo reductive desulfurization to give 4-iminoimidazolidin-2-one 11a and the methyl analog 11d, respectively.
Databáze:	OpenAIRE
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