New synthetic reaction by electrolysis malonic acid as a ketone synthon

✍ Scribed by Junzo Nokami; Toshiyuki Yamamoto; Mikio Kawada; Mari Izumi; Nobuko Ochi; Rokuro Okawara

• Book ID: 104238520
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 126 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87187-2

✦ Synopsis

Malonic acid derivatives(gem-dicarboxylic acids) were converted to the corresponding ketones by the electrolysis. The reaction was employed for the synthesis of jasmones.

Various ketone synthons which are equivalent to carbonyl dianion have been applied for organic synthesis. However, a useful synthetic reaction associated with the last one has not been reported. 4) EC=0 =

;c=;X 1) e&b 2)

3. e /cOOH t 8 'SO-, e(fse 'COOH, e"COOH We have resently reported that a-phenylthio(or a-methylthio)carboxylic acid can function as a ketone synthon by anodic oxidation reaction. 5) This finding suggests us that the malonic acid may function as a ketone synthon by electrolysis.