The Transformations of Thiols and their Dimers in the Redox-Mediated Thiol-Disulfide Exchange Reaction
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
The Transformations of Thiols and their Dimers in the Redox-Mediated Thiol-Disulfide Exchange Reaction
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| Автор |
Burmistrova, D. A.
Smolyaninov, I. V. Berberova, N. T. |
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| Тематика |
INDUSTRIAL WASTE
THIOLS THIOL-DISULFIDE EXCHANGE UNSYMMETRICAL DISULFIDES REDOX-MEDIATOR ELECTROCHEMISTRY |
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| Описание |
The utilization of n-alkanethiols and their dimers (C3, C4) during the promoted thiol-disulfide exchange under electrochemical conditions is considered.
A number of redox-mediators were studied as promoters of the thiol-disulfide exchange reaction. Thiol-disulfide exchange reactions lead to the formation of unsymmetrical disulfides. Unsymmetrical arylalkyl disulfides with anisole or veratrol fragments were obtained with a high yield (up to 97%). Received: 09.12.23. Revised: 19.12.23. Accepted: 20.12.23. Available online: 29.12.23. A search for new approaches to sulfurous waste utilization is one of the urgent tasks of chemical technology. Thiol-disulfide exchange reaction (TDE) is one f the possible ways to involve technogenic wastes in organic synthesis. Electricity can promote such type of interactions. In this paper, we have studied TDE reactions involving low molecular weight thiols or their dimers under electrochemical conditions. The exchange processes were examined using the model reaction between 1-propanethiol and phenyl disulfide. Electrolysis was performed in the presence of redox mediators such as arylphosphines, substituted amines, o-, p-aminophenols or catechol. These compounds can initiate a TDE process with a formation of unsymmetrical disulfides. 4-Amino-2,6-diphenylphenol was chosen as the most effective redox mediator, which reduces the anodic overvoltage of a thiol oxidation by 1.20 V. The advantage of electrolysis in an undivided cell is the increased yield of target unsymmetrical disulfides due to the possibility of reduction ofhomodimers at the cathode. The involvement of refining waste, such as C3–C4 disulfide oil, in the reaction with substituted thiophenols made it possible to obtain a number of unsymmetrical arylalkyl disulfides with biologically active fragments in a high yield (up to 97%) under indirect electrolysis conditions. This work was supported by the Grant for the young PhD scientists МК-2488.2022.1.3 (agreement No. 075-15-2022-526) https://grants.extech.ru/. |
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| Дата |
2024-01-18T12:45:24Z
2024-01-18T12:45:24Z 2023 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) Published version (info:eu-repo/semantics/publishedVersion) |
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| Идентификатор |
Burmistrova D. A. The Transformations of Thiols and their Dimers in the Redox-Mediated Thiol-Disulfide Exchange Reaction / D. A. Burmistrova, I. V. Smolyaninov, N. T. Berberova // Chimica Techno Acta. — 2023. — Vol. 10, No. 4. — № 202310418.
2411-1414 http://elar.urfu.ru/handle/10995/129337 https://www.elibrary.ru/item.asp?id=60040562 10.15826/chimtech.2023.10.4.18 |
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| Язык |
en
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| Связанные ресурсы |
Chimica Techno Acta. 2023. Vol. 10. № 4
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| Формат |
application/pdf
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| Издатель |
Уральский федеральный университет
Ural Federal University |
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