Oxidative N-Dealkylation of Tertiary Amines with Tetraethylammonium Periodate Catalyzed by Metal Complexes

Abstract

The oxidative N-dealkylation of tertiary amines, N,N-dimethylaniline and N,N-diethylaniline, catalyzed by some sterically hindered FeIII complexes and tetraethylammonium periodate as oxidant gave the corresponding N-dealkylated and mono-oxygenated products in good yields. The presence of electronegative atoms on the catalyst complexes influenced the product yield. The presence of H-atom abstractor 2,6-di-tert-butyl-4-methylphenol did not influence product formation, thereby suggesting that the reaction proceeded predominantly via a one-electron transfer mechanism rather than via hydrogen abstraction. Tetraethylammonium periodate favoured oxygen transfer to the substrate.