Is the electrocatalytic epoxidation of stilbene isomers using manganese (III) tetradentate Schiff bases complexes stereoselective?

Three manganese (III) complexes were obtained with H2Salen derivatives and used as catalysts in the epoxidation reactions of E- and Z-stilbene isomers. The preparative electrolyses were carried out at 25 °C in acetonitrile solution containing 0.1 M TBAP, 10−3 M complex, 10−2 M 2-methylimidazole and 0.1 M benzoic anhydride plus stilbene as substrate. Our results showed clearly that E-stilbene was totally converted to Z-stilbene oxide whereas Z-stilbene leads to a mixture in which the benzaldehyde was the major by-product. In our experimental conditions, the turnovers recorded for different experiments were located in the 3.7–6.6 range.