Electrochemical carboxylation of ketene S,S-acetals

The cathodic reduction of ketene S,S-acetals in aprotic media has been investigated. Because of instability of the radical anion the reduction steps are irreversible. In presence of carbon dioxide the half-wave potentials are shifted to more positive values and preparative scale electrolysis yields...

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Bibliographic Details
Published in:Electrochimica acta 1985-01, Vol.30 (2), p.155-157
Main Authors: Rüttinger, H.H., Rudorf, W.-D., Matschiner, H.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Summary:The cathodic reduction of ketene S,S-acetals in aprotic media has been investigated. Because of instability of the radical anion the reduction steps are irreversible. In presence of carbon dioxide the half-wave potentials are shifted to more positive values and preparative scale electrolysis yields 2-alkylthio-3-acyl-acrylic acids. The pathway of the electrochemical substitution is discussed as subsequent addition and elimination steps.
ISSN:0013-4686
1873-3859
DOI:10.1016/0013-4686(85)80076-1