Supercritical carbon dioxide in organometallic synthesis: Combination of sc-CO2 with Nafion film as a novel reagent in the synthesis of ethers from hydroxymethylmetallocenes

Metallocenyl carbinols FcCH2OH (1a) and RcCH2OH (1b) dissolved in sc-CO2 penetrate into the acidic Nafion film under 20 MPa and 80 or 35 °C. After removal of pressure and leaving at room temperature, the crystals rapidly formed on the surface of the film, were identified as ethers McCH2OCH2Mc, Mc = Fc or Rc, by X-ray study. Mechanism of their formation is discussed.

Graphical abstractMetallocenyl carbinols FcCH2OH (1a) and RcCH2OH (1b) dissolved in sc-CO2 in the presence of acidic Nafion film under 20 MPa after removal of pressure and leaving at room temperature afforded the crystals rapidly formed on the surface of the film identified as ethers McCH2OCH2Mc, Mc = Fc or Rc by X-ray study. Mechanism of their formation is discussed.Figure optionsDownload full-size imageDownload as PowerPoint slide