Synthesis of Aryl 3,5-Dinitrophenyl Sulfones and Sulfoxides. Transformations of 3,5-Dinitrodiphenyl Sulfone in Reactions with O- and S-Nucleophiles

Autor:	Olga V. Serushkina, Mikhail D. Dutov, Svyatoslav A. Shevelev, O. Yu. Sapozhnikov, Bogdan I. Ugrak
Rok vydání:	2003
Předmět:	Substitution reaction chemistry.chemical_compound chemistry Nucleophile Aryl Nitro Nucleophilic substitution Organic chemistry General Medicine Benzene Hydrogen peroxide Medicinal chemistry Sulfone
Zdroj:	ChemInform. 34
ISSN:	1522-2667 0931-7597
Popis:	1-Arylthio-3,5-dinitrobenzenes are selectively oxidized to the corresponding sulfones and sulfoxides by the action of hydrogen peroxide. Reactions of 3,5-dinitrodiphenyl sulfone with O- and S-centered nucleophiles (RXH, X = O, S) in dipolar aprotic solvents in the presence of K2CO3 result in replacement of the nitro group by the RX fragment; the reaction with methanol occurs in aqueous medium in the presence of NaHCO3. Substitution of the nitro group in 3,5-dinitrodiphenyl sulfone by phenylthio group, followed by oxidation of the sulfur atom to SO2 and further replacement of the remaining nitro group yields 1,3,5-tris(phenylsulfonyl)benzene. The phenylsulfonyl group in the latter is replaced by phenylthio group by reaction with PhSH in the presence of K2CO3. Mononitrosulfones obtained by nucleophilic substitution in the title compound can be reduced to the corresponding anilines.
Databáze:	OpenAIRE
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