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Molecules 2013, 18(11), 13754-13768; doi:10.3390/molecules181113754

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

*  and
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)
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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.
Keywords: natural compounds oxidation; hydrogen peroxide; methyltrioxorhenium natural compounds oxidation; hydrogen peroxide; methyltrioxorhenium
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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