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Molecules 2013, 18(11), 13754-13768;

Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium

Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, Catania 95125, Italy
Author to whom correspondence should be addressed.
Received: 17 September 2013 / Revised: 24 October 2013 / Accepted: 25 October 2013 / Published: 7 November 2013
(This article belongs to the Section Natural Products Chemistry)
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We have investigated the oxidative behaviour of natural compounds such as methyl 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 regio- and 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. View Full-Text
Keywords: natural compounds oxidation; hydrogen peroxide; methyltrioxorhenium natural compounds oxidation; hydrogen peroxide; methyltrioxorhenium

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Amato, M.E.; Ballistreri, F.P.; Pappalardo, A.; Tomaselli, G.A.; Toscano, R.M.; Sfrazzetto, G.T. Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium. Molecules 2013, 18, 13754-13768.

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