We have investigated the oxidative behaviour of natural compounds such asmethyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5),methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H2O2/pyridine. The reactions, performed in CH2Cl2/H2O at 25 °C, have shown good regioandstereoselectivity. The oxidation products were isolated by HPLC or silica gelchromatography and characterized by MS(EI), 1H-, 13C-NMR, APT, gCOSY, HSQC,TOCSY and NOESY measurements. The selectivity seems to be controlled by thenucleophilicity of double bonds and by stereoelectronic and steric effects.
Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
AMATO, Maria Emanuela;BALLISTRERI, Francesco Paolo;PAPPALARDO, ANDREA;TOMASELLI, Gaetano;TOSCANO, Rosa Maria;TRUSSO SFRAZZETTO, GIUSEPPE
2013-01-01
Abstract
We have investigated the oxidative behaviour of natural compounds such asmethyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5),methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H2O2/pyridine. The reactions, performed in CH2Cl2/H2O at 25 °C, have shown good regioandstereoselectivity. The oxidation products were isolated by HPLC or silica gelchromatography and characterized by MS(EI), 1H-, 13C-NMR, APT, gCOSY, HSQC,TOCSY and NOESY measurements. The selectivity seems to be controlled by thenucleophilicity of double bonds and by stereoelectronic and steric effects.| File | Dimensione | Formato | |
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