Stereochemistry of copper- and nickel-catalyzed insertion of carbon dioxide into epoxides. A microwave study

✍ Scribed by Jan-E. Bäckvall; Ola Karlsson; Stig O. Ljunggren

• Publisher: Elsevier Science
• Year: 1980
• Tongue: French
• Weight: 242 KB
• Volume: 21
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71172-5

✦ Synopsis

Reaction of trans-1,2_dideuterioethene oxide (1) with carbon dioxide, using copper and nickel catalysts, and subsequent analysis of the product ethene carbonate-d2 (2) by microwave spectroscopy, shows that the copper-catalyzed reaction is stereospecific (retention) whereas the nickel-catalyzed reaction is non-stereospecific.

The activation of carbon dioxide and its transfer to organic substrates by means of transition metals is a matter of current interest. Recently it has been found that copper(I)'-and nickel(O)'-complexes catalyze the insertion of carbon dioxide into epoxides to yield the corresponding alkene carbonates (eq. 1). Little is known about the role of the transition metal in these reactions, but an oxometallacyclobutane (cf. 2) has been suggested as a possible intermediate in the nickel-catalyzed reaction. 2,3