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Oxidation reactions of bis(heteroaryl)methanes to the corresponding ketones were investigated in the absence of usual oxidation reagents and catalysts. There are strong indications that the reaction pathway involves radical species. The spontaneous oxidation of bis(heteroaryl)carbinols was also investigated by kinetic measures. Strong base catalysis, together with relevant hydrogen/deuteron isotopic effect, were observed. Both reaction pathways, from methane derivatives and from carbinols derivatives, involve the presence of a tautomeric equilibrium of the considered heterocycles.

Spontaneous oxidation of bis(heteroaryl)methanes and bis(heteroaryl)carbinols to ketones