Oxidations of organic compounds by cobaltic salts. Part XIV. Oxidations of some aliphatic amines and α-amino-acids

Abstract

Kinetic and product studies have been made in aqueous perchloric acid solution with two amines and six amino-acids. In excess of acid butylamine and benzylamine are oxidised very slowly by cobalt(III). The reaction is considered to occur by direct outer-sphere attack of the cobaltic ion on the hydrocarbon skeleton of the amine. α-Amino-acids are oxidised more rapidly, i.e., at a rate comparable with that for oxidation of other carboxylic acids (Parts VI, XI–XIII). The oxidation mechanism is also similar since the amino-acids degrade to ammonia and the corresponding aldehydes and thence to more highly oxidised products. R·CH(NH₂)·CO₂H → R·CHO + NH₃+ CO₂