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EPR of free radicals formed from 3-hydroxyesculetin and related derivatives

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EPR spectroscopy of 3-hydroxyesculetin (1, solid and in solution) and of the radicals formed during the aerobic oxidation of alkaline solutions of 1 and related compounds was investigated. 1 in the solid state was studied by pulsed EPR experiments and showed a radical character. The aerobic oxidation of alkaline solutions of 1 was also followed by EPR spectroscopy. A ring contraction occurred leading to a 5,6-dihydroxybenzofuran-2-carboxylate radical. The autoxidation of an alkaline solution of (Z)-3-(3,4-dihydroxyphenyl)-2-hydroxypropenoic acid allowed the observation of a spectrum attributable to 5,6-dihydroxybenzofuran-3-one-2-carboxylate radical. The formation mechanisms of these radicals are discussed.


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