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 |
|