Electrochemical method to vinyl fluorides (II). Cathodic cleavage and carboxylation of 1-fluoro-2-(4-biphenylyl)vinyl phenyl sulphoxide in nonaqueous media

Add time:07/30/2019    Source:sciencedirect.com

The electrolytic reduction of 1-fluoro-2-(4-biphenylyl)vinyl phenyl sulphoxide (1) in nonaqueous media involves desulphinylation, defluorination followed by reduction of the sulphinyl group, and reduction to the corresponding sulphide, resulting in the formation of 1-fluoro-2-(4-biphenylyl)ethylene (2), 2-(4-biphenylyl)vinyl phenyl sulphide (3) and 1-fluoro-2-(4-biphenylyl)vinyl phenyl sulphide (4). Distribution of these products is greatly dependent on the proton donors such as phenol, acetic acid and benzoic acid. In the absence of proton donors, the yields of products are low. The controlled potential electrolysis of 1 in N,N-dimethylformamide containing carbon dioxide was subjected to a substituting carboxylation to afford 2-fluoro-3-(4-biphenylyl)-propenoic acid (6), with concomitant formation of 2 and 3.

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