Intramolecular anodic olefin coupling reactions: the use of allylsilanes

✍ Scribed by Kevin D. Moeller; Christine M. Hudson

• Book ID: 104216275
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 301 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79910-2

✦ Synopsis

The use of allylsilanes as directing groups in the intramolecular electrochemical coupling of electron rich olefins has been examined. The allylsilanes were shown to provide an effective means for controlling product selectivity, and led to the formation of five-and six-membered ring products in 59-84% isolated yields.

Recently, we reported that the intramolecular coupling of electron-rich olefins can be accomplished with the use of an anodic oxidation reaction? These cyclizations were effectively initiated by the oxidation of alkyl and silyl enol ethers, and terminated with the use of styrenes, simple alkyl olefins, and enol ethers. Although the use of simple alkyl-substituted olefins held promise as a general means of carbon-carbon bond formation, these reactions often led to mixtures of products. This problem was particularly acute when a disubstituted olefin was employed as the terminating group. For example, the anodic oxidation of 1 at a platinum anode under constant current conditions led to the formation of three cyclized products in approximately equal yields.

Oh?

This electrode material was purchased from The Electrosynthesis Co., Inc.