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

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/H(2)O(2)/pyridine. The reactions, performe...

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Detalles Bibliográficos
Autores principales: Amato, Maria E., Ballistreri, Francesco P., Pappalardo, Andrea, Tomaselli, Gaetano A., Toscano, Rosa M., Sfrazzetto, Giuseppe Trusso
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270049/
https://www.ncbi.nlm.nih.gov/pubmed/24213654
http://dx.doi.org/10.3390/molecules181113754
Descripción
Sumario: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/H(2)O(2)/pyridine. The reactions, performed in CH(2)Cl(2)/H(2)O 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), (1)H-, (13)C-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.

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