Abstract

The electrochemical oxidation of 9-methylxanthine proceeds via four voltammetric oxidation peaks at the pyrolytic graphite electrode. The first voltammetric oxidation peak (peak Ia) is a 1e reaction giving a radical which dimerizes to 8,8′-bi-9-methyl-9H-purine-2,6-(1H, 3H)-dione. Peak IIa is a further 2e electrooxidation of the peak Ia dimer to another yellow dimer 8,8′-bi-9-methyl-9H-purine-2,6-(1H)-dione-3,5-(3H)-diiminylidene. This dimer is not very stable and it hydrolyzes to 1-methyl allantoin. Peak IIIa is an adsorption pre-peak to peak IVa which corresponds, overall, to a direct 4e−4H+ electrooxidation of 9-methylxanthine to an unstable diimine of 9-methyluric acid. Hydrolysis of this diimine leads to a variety of ultimate products.

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