Related Experiment Video
Updated: May 6, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium
Maria E Amato1, Francesco P Ballistreri, Andrea Pappalardo
1Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, Catania 95125, Italy. rmtoscano@unict.it.
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.
Related Concept Videos
Regioselectivity of Electrophilic Additions-Peroxide Effect
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Radical Anti-Markovnikov Addition to Alkenes: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Hydroboration-Oxidation of Alkenes
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...

