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dc.contributor.author | Devyatova N. | |
dc.contributor.author | Kurbangalieva A. | |
dc.contributor.author | Yanilkin V. | |
dc.contributor.author | Chmutova G. | |
dc.date.accessioned | 2018-09-18T20:17:32Z | |
dc.date.available | 2018-09-18T20:17:32Z | |
dc.date.issued | 2009 | |
dc.identifier.issn | 1066-5285 | |
dc.identifier.uri | https://dspace.kpfu.ru/xmlui/handle/net/138376 | |
dc.description.abstract | The electrochemical oxidation of aryl- and alkylthio derivatives of mucochloric acid (3,4-dichloro-5-hydroxyfuran-2(5H)-one) in MeCN-Bu 4NBF4 (0.1 mol L-1) was investigated. It was shown that all sulfides are electrochemically active, from one to five oxidation steps of sulfur-containing groups were observed for them. The ease and direction of oxidation of the thio group depend on its nature and position in the furanone ring. 3-Substituted 2(5H)-furanones possess the lowest oxidation potential. 4-Substituted 2(5H)-furanones are predominantly oxidized to sulfoxides, 5-aryl- and -alkylthio derivatives undergo fragmentation to give mucochloric acid, and 3-arylthio derivative gives complex unidentified mixture of products. In the case of 3,4-bis(4-methylphenylthio) derivative, the oxidation product of the arylthio group at the 3 position to the corresponding sulfoxide was isolated. Based on the data from cyclic voltammetry with different concentrations of a substrate and water added, the results of preparative electrolysis and quantum chemical calculations, possible mechanisms of electrochemical oxidation of mucochloric acid-derived sulfides are discussed. The initial common step is a reversible single-electron transfer from the substrate molecule to form highly reactive radical cation. © 2009 Springer Science+Business Media, Inc. | |
dc.relation.ispartofseries | Russian Chemical Bulletin | |
dc.subject | Electrochemical oxidation | |
dc.subject | Fragmentation | |
dc.subject | Furan-2(5H)-ones | |
dc.subject | Mucochloric acid | |
dc.subject | Quantum chemistry | |
dc.subject | Sulfides | |
dc.subject | Sulfoxide | |
dc.title | Electron transfer and subsequent reactions during electrochemical oxidation of aryl- and alkylthio derivatives of mucochloric acid | |
dc.type | Article | |
dc.relation.ispartofseries-issue | 5 | |
dc.relation.ispartofseries-volume | 58 | |
dc.collection | Публикации сотрудников КФУ | |
dc.relation.startpage | 908 | |
dc.source.id | SCOPUS10665285-2009-58-5-SID77955742895 |