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)]
authors Bruno, SM; Gomes, AC; Abrantes, M; Valente, AA; Pillinger, M; Goncalves, IS
nationality International
journal JOURNAL OF ORGANOMETALLIC CHEMISTRY
author keywords Molybdenum carbonyl complexes; Acid catalysis; Epoxides; Ring-opening reactions; Isomerization; Alchoholysis
keywords ALPHA-PINENE OXIDE; ORGANOMETALLIC LEWIS-ACIDS; ISOMERIZATION; CATALYST; MOLYBDENUM(II); ALCOHOLYSIS; CHEMISTRY; CHEMICALS
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.
publisher ELSEVIER SCIENCE SA
issn 0022-328X
year published 2015
volume 799-800
beginning page 179
ending page 183
digital object identifier (doi) 10.1016/j.jorganchem.2015.09.022
web of science category Chemistry, Inorganic & Nuclear; Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000366589600025
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journal analysis (jcr 2017):
journal impact factor 1.946
5 year journal impact factor 1.871
category normalized journal impact factor percentile 53.567
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