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)]


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.



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Bruno, SM; Gomes, AC; Abrantes, M; Valente, AA; Pillinger, M; Goncalves, IS

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This work was developed in the scope of the project CICECO-Aveiro Institute of Materials [FCT (Fundacao para a Ciencia e a Tecnologia) ref. UID/CTM/50011/2013], financed by national funds through the FCT/MEC and when applicable co-financed by FEDER (Fundo Europeu de Desenvolvimento Regional) under the PT2020 Partnership Agreement. We acknowledge funding by FEDER through COMPETE (Programa Operacional Factores de Competitividade) and by national funds through the FCT within the project FCOMP-01-0124-FEDER-029779 (FCT ref. PTDC/QEQ-SUP/1906/2012, including the research grant with ref. BPD/U189/4864/2013 to A.C.G.). The FCT and the European Union are acknowledged for a post-doctoral grant to S.M.B. (ref. SFRH/BPD/46473/2008) co-funded by MCTES and the European Social Fund through the program POPH of QREN.

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