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

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

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Received: 17 September 2013; in revised form: 24 October 2013 / Accepted: 25 October 2013 / Published: 7 November 2013
(This article belongs to the Section Metabolites)
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Abstract: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Amato ME, Ballistreri FP, Pappalardo A, Tomaselli GA, Toscano RM, Sfrazzetto GT. Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium. Molecules. 2013; 18(11):13754-13768.

Chicago/Turabian Style

Amato, Maria E.; Ballistreri, Francesco P.; Pappalardo, Andrea; Tomaselli, Gaetano A.; Toscano, Rosa M.; Sfrazzetto, Giuseppe T. 2013. "Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium." Molecules 18, no. 11: 13754-13768.


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