title: Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium.
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.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, Catania 95125, Italy. rmtoscano@unict.it.
authors.forename: Maria E
authors.initials: ME
authors.lastname: Amato
authors.forename: Francesco P
authors.initials: FP
authors.lastname: Ballistreri
authors.forename: Andrea
authors.initials: A
authors.lastname: Pappalardo
authors.forename: Gaetano A
authors.initials: GA
authors.lastname: Tomaselli
authors.forename: Rosa M
authors.initials: RM
authors.lastname: Toscano
authors.forename: Giuseppe Trusso
authors.initials: GT
authors.lastname: Sfrazzetto
mesh_terms: D006861:Hydrogen Peroxide / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D009942:Organometallic Compounds; C411866:methyltrioxorhenium VII; D006861:Hydrogen Peroxide