Sodium hypochlorite as a selective oxidant for organic compounds

TLDR: In this paper, a study of the reactions of sodium hypochlorite with a wide variety of compounds has been carried out, and a new methodology of oxidation has been developed for structural elucidation of complex materials such as coal.

Abstract: A study of the reactions of sodium hypochlorite with a wide variety of compounds has been carried out. The data indicate that a structure capable of producing a carbanion stable enough to undergo halogenation is oxidized by sodium hypochlorite to a ketone or a carboxylic acid. How far the oxidation will proceed is determined by enolateion resonance stabilization and by inductive and steric effects of the activating group (e.g.CO, –NO2, –CN, or –CO2H). Unactivated aromatic, hydroaromatic, alicyclic, and alkane systems are not oxidized. Heteroaromatic ring systems capable of undergoing azomethine-type addition can readily be cleaved, whereas benzenoid ring systems undergo no change. Oxidation of an activated alicyclic compound containing a tertiary sp3 carbon system may result in loss of one, two, or three carbon atoms as CO2 or CHCl3via 1,3- and 1,4-halogenation steps. Based on this investigation, a new methodology of oxidation has been developed for structural elucidation of complex materials such as coal.