Ring-opening of epoxides promoted by organomolybdenum complexes of the type [eta(5)-C5H4R)mo(CO)(2)(773-C3H5)] and [(eta(5)-C5H5) Mo(CO)(3)(CH2R)]

Abstract

The cyclopentadienyl molybdenum carbonyl complexes [(775-05H(4)R)Mo(CO)(2)(773-C3H5) and [(eta(5)-C5H5) Mo(CO)(3)(CH2R)] (R = H, COOH) have been shown to promote acid-catalysed reactions in liquid phase, under moderate conditions. The catalytic alcoholysis of styrene oxide with ethanol at 35 degrees C gave 2ethoxy-2-phenylethanol in 100% yield within 30 min for the dicarbonyl complexes and 3-6 h for the tricarbonyl complexes. Steady catalytic performances were observed in consecutive runs with the same catalytic solution, suggesting fairly good catalytic stability. In the second acid-catalysed reaction studied, the isomerization of a-pinene oxide at 55 degrees C gave campholenic aldehyde and trans-carveol in a total yield of up to 86% at 100% conversion. Chemoselectivity is shown to be solvent dependent. (C) 2015 Elsevier BY. All rights reserved.