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

✍ Scribed by Akira Kunugi; Shinya Mori; Seiji Komatsu; Hiroshi Matsui; Hidemitsu Uno; Katsuji Sakamoto

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 845 KB
• Volume: 40
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(94)00367-a

✦ Synopsis

The electrolytic reduction of 1-fluoro-2-(4-biphenyiyi)vinyi phenyi suiphoxide (1) in nonaqueous media involves desuiphinylation, defluorination followed by reduction of the suiphinyi group, and reduction to the corresponding suiphide, resulting in the formation of I-fluoro-2-(4_biphenyiyi)ethylene (4 2-(4-biphenyiyi)vinyi phenyl suiphide (3) and I-fluoro-2-(~biphenyiyi)vinyi phenyi suiphide (4).

Distribution of these products is greatly dependent on the proton donors such as phenol, acetic acid and benxoic acid. In the absence of proton donors, the yields of products are low. The controlled potential electrolysis of 1 in ~,~~imethyifo~amide containing carbon dioxide was subjected to a substituting car~xylation to afford 2-fluoro-3~~biphenylyl)-pro~oi~ acid (41, with concomitant formation of 2 and 3.