The oxidation of the para-nitrophenylhydrazones, derived from the (3- ketoester ethyl acetoacetate and its derivatives, using lead tetraacetate (LTA) and mercuric acetate (MA) were studied. The oxidation products isolated were the azoacetate and, in some cases, the azoalkene. The product formed was found to depend, to a large extent, on the choice of solvent. Oxidation of the hydrazone in acidic medium resulted in azoacetate formation while azoalkene was formed in neutral medium. Azoacetate formation could be ensured, irrespective of solvent used, by replacing the labile hydrogens on the carbon alpha to the ester group, with methyl groups. Initial studies involving replacement of the hazardous metallic oxidising agents by iodobenzene diacetate (IBA) have proved successful. We report the first use of IBA as a route to obtaining azoacetates. A number of azoacetates isolated were further reacted with base in alcoholic medium, in the presence of a catalyst. Among the products isolated was a tertiary amide which was conclusively identified using X-ray crystallography. The mechanism by which this tertiary amide was arrived at was studied in some detail. The possibility of an intermediate azocarbinol was addressed and results indicate this may not be the case. Further studies involving addition reactions and cross-over experiments indicate a concerted one step carbon to nitrogen acetyl migration followed by rearrangement. This novel rearrangement was extended to a number of azoacetate derivatives, and NMR temperature dependent studies were carried out on the resulting rearranged species which exhibited characteristic resonances for amides and nitrogen inversion. A selection of these tertiary amides were considered as possible aza-plactam precursors. While there is a proliferation of literature on p-lactams these cyclic dinitrogen analogues have received little attention. In a number of cases, the tertiary amides isolated, were successfully cyclised to novel aza-p-lactams, which may prove to be active antibacterical agents. The work has been reported as a preliminary communication (see appendix).