Anodic behaviour of unsaturated systems—I. Oxidation of some enol ethers: alkyl (aryl) oxy-3 propenonitriles

✍ Scribed by Marie-Armelle le Moing; Georges le Guillanton; Jacques Simonet

• Publisher: Elsevier Science
• Year: 1981
• Tongue: English
• Weight: 526 KB
• Volume: 26
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(81)80015-1

✦ Synopsis

Enol ethers corresponding to the title compounds am oxidized at a platinum or glassy carbon anode in acetonitrile. In poorly nucleophilic media, the electrochemical reaction principally leads to dimers and oligomers due to the electrophilic attack of transient cations on the aromatic substituents of the ethylenic double bond. On the other hand, in the presence of efficient nucleophiles, the anodic reaction may appear to he more selective (at least in certain cases) and the product distribution demonstrates the formation of an intermediate epoxonium ion after the transfer of two electrons. In all media, reactions are furthermore discussed according to the nature of the substituents of the enol ether double bond.