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Electrochemical behaviour of some 3-methylthio-1,2-dithiolium cations in dimethylformamide solution
Substituted 3-methylthio-1,2-dithiolium cations were prepared by alkylation of the corresponding 1,2-dithiole-3-thiones. These compounds were easily reduced in DMF at a mercury electrode, following two one-electron waves. Electrolysis, carried out at a mercury pool electrode and followed by an alkyl...
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Published in: | Electrochimica acta 2005-04, Vol.50 (11), p.2219-2225 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Substituted 3-methylthio-1,2-dithiolium cations were prepared by alkylation of the corresponding 1,2-dithiole-3-thiones. These compounds were easily reduced in DMF at a mercury electrode, following two one-electron waves. Electrolysis, carried out at a mercury pool electrode and followed by an alkylation or an acylation, provided the corresponding alkyl (or acyl) dithioesters and by-products. At a platinum or glassy carbon electrode the reduction was an irreversible process, which was dependent upon the cathode nature. Whatever the electrode, the reduction was a combination of two reactions, a two-electron reduction and a one-electron one involving a dimerization. The electrochemical behaviour of 3-methylthio-1,2-dithiolium cations exhibited many analogies with the cathodic behaviour of the corresponding 1,2-dithiole-3-thiones. Moreover, identical intermediates were implicated in the reduction of 3-methylthio-1,2-dithiolium cations and in the reductive alkylation of 1,2-dithiole-3-thiones. |
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ISSN: | 0013-4686 1873-3859 |
DOI: | 10.1016/j.electacta.2004.10.004 |