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

EPR of free radicals formed from 3-hydroxyesculetin and related derivatives 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Brill Academic Publishers
Copyright
Copyright © 2003 by VSP 2003
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856703765694318
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 17, 2004

References

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