Abstract

In dihydrouracil a reversible free radical conversion between the two hydrogen-abstraction radicals 5-yl and 6-yl has been found. Thus, the 6-yl to 5-yl transformation takes place if an irradiated sample is cooled below 220 K and exposed to light with wavelengths below 450 nm. The reverse process is initiated by a subsequent heating of the sample. The kinetics for both the light- and temperature-induced processes have been studied. The results indicate that an intramolecular hydrogen transfer process is more probable than a corresponding intermolecular one. Comparison is made with other unsaturated and saturated pyrimidine derivatives.

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