Oxidation by persulphate. Part IV. Silver-catalysed oxidation of primary aliphatic amines
Abstract
Oxidation of a primary aliphatic amine, RCH2·NH2, by aqueous persulphate under alkaline conditions and in the presence of a catalytic amount of silver nitrate, gave the aldimine, RCH:N·CH2R, which was subsequently hydrolysed to the aldehyde, RCHO, and the original amine, or was hydrogenated to the corresponding secondary amine, (RCH2)2NH. The yield of aldehyde varied from 15 to 95% among C3—C9 amines, and the conversion was favoured by branching in the alkyl chain or by the presence of an α-phenyl group. Under similar conditions, a primary amine of the type R1R2CH·NH2 was converted into the ketone, R1R2CO, without separation of the ketimine. Primary amines of the type R1R2R3C·NH2 were unchanged. Secondary reactions may complicate the oxidations.
Please wait while we load your content...
