Cetyldimethyl benzyl ammonium cerium nitrate as a phase-transfer oxidant in the oxidation of alcohols to carbonyl compounds

Abstract

Oxidation of organic substrates by inorganic reagents is restricted by mutual insolubility of the two. However, this problem of mutual insolubility can be alleviated by the use of oxidants in the form of phase transfer reagents, like tetra-alkylammonium salts. Tetra-alkylammonium salt has a polar (N+) group and hydrocarbon side chains (alkyl groups). The ammonium salt allows a low concentration of oxidant to pass into the organic layer where they act as oxidizing agent. In the present case, the synthesis of a phase transfer oxidant cetyldimethyl benzyl ammonium cerium nitrate (CDBACN) and its use in the oxidation of alcohols to carbonyl compounds has been reported. CDBACN was synthesized from cetyldimethyl benzyl ammonium chloride (CDBACl) and ammonium ceric nitrate (CAN). The reagent was characterized by elemental analysis and spectral studies. The solubility and electronic spectra of the oxidant in various solvents were studied. This oxidant was successively utilized in the oxidation of different alcohols.