Oxidation of aryldialkylamines with cerium(IV) ammonium nitrate and thailium(III) nitrate

Abstract

Nine alkylmethylanilines were oxidised with cerium(IV)ammonium nitrate and thallium(III) nitrate in acetic acid, acetonitrile, and methanol. Reaction products were those deriving from demethylation, dealkylation, and aromatic nitration at positions ortho and para to the amino-group. The ratio between demethylation and dealkylation and between them and aromatic nitration is discussed in terms of (i) the oxidising power and electrophilicity of the reagent and (ii) the co-ordinative properties of the solvent.