Electron spin resonance study of radicals obtained from the oxidation of naturally occurring hydroxypyrones

Abstract
Many hydroxylated derivatives of γ-pyrone such as kojic acid, maltol, flavones, and also coumarins, may be oxidised by CeIV in acidic solutions to give radicals analogous to phenoxyl radicals. These have been observed by e.s.r. spectroscopy: the patterns of coupling constants obey some simple rules which are given in terms of non-bonding orbital coefficients. Addition of ·OH to 4-hydroxy-6-methylpyran-2-one gives a novel type of radical, 2,3,4-trihydroxy-6-methylpyranyl, whose structure is confirmed theoretically.

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