412274-54-5Relevant articles and documents
Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium
Amato, Maria E.,Ballistreri, Francesco P.,Pappalardo, Andrea,Tomaselli, Gaetano A.,Toscano, Rosa M.,Sfrazzetto, Giuseppe Trusso
, p. 13754 - 13763 (2013)
We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), a-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 regioand stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), 1H-, 13C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.