Homogeneous green catalysts for olefin oxidation by mono oxovanadium(V) complexes of hydrazone Schiff base ligands

Three mono oxovanadium(V) complexes of tridentate Schiff base ligands [VO(OMe)L-1] (1), [VO(OMe)L-2] (2) and [VO(OMe)L-3] (3) obtained by monocondensation of 3-hydroxy-2-naphthohydrazide and aromatic o-hydroxyaldehydes have been synthesized (H2L1 = (E)-3-hydroxy-N '-(2-hydroxy-3-methoxybenzylidene)- 2-naphthohydrazide, H2L2 = (E)-3-hydroxy-N '-(2-hydroxybenzylidene)-2-naphthohydrazide and H2L3 = (E)-N '-(5-bromo-2-hydroxybenzylidene)-3-hydroxy-2-naphthohydrazide). The complexes were characterized by spectroscopic methods in the solid state (IR) and in solution (UV-Vis, H-1 NMR). Single crystal X-ray analyses were performed with 1 and 2. The catalytic potential of these complexes has been tested for the oxidation of cyclooctene using H2O2 as the terminal oxidant. The effects of various parameters including the molar ratio of oxidant to substrate, the temperature, and the solvent have been studied. The catalyst 2 showed the most powerful catalytic activity in oxidation of various terminal, cyclic and phenyl substituted olefins. Excellent conversions have been obtained for the oxidation of cyclic and bicyclic olefins. (C) 2010 Elsevier B.V. All rights reserved.