Oxidation of m-Phenoxytoluene with Ceric Trifluoroacetate

Article abstract of DOI:10.1021/jo00157a021

Ceric trifluoroacetate in aqueous trifluoroacetic acid has been found to be especially effective for the oxidation of activated toluenes to the corresponding aldehydes.Ceric ion is consumed in stoichiometric amounts but can be regenerated electrochemically at high current efficiencies (95 percent).A detailed study of the oxidation of m-phenoxytoluene to m-phenoxybenzaldehyde is presented.A study of the reaction mechanism, which involves both cations and radical cations, led to a choise of cosolvents which stabilize these intermediates and thus increase the yield of aldehyde formation.