Co-Authors:
Rosenthal, I., Laboratory of Pathophysiology, National Cancer Institute, National Institutes of Health, Bethesda, MD 20205, United States
Mossoba, M.M., Laboratory of Pathophysiology, National Cancer Institute, National Institutes of Health, Bethesda, MD 20205, United States
Riesz, P., Laboratory of Pathophysiology, National Cancer Institute, National Institutes of Health, Bethesda, MD 20205, United States
Abstract:
The photochemical reactions of dibenzoyl peroxide with some organic compounds were found by EPR and spin-trapping to generate free radicals in dimethyl sulfoxide solutions at room temperature. Two reaction mechanisms occur which determine the structures of the radicals generated. The first involves a one-electron oxidation and the second a hydrogen atom transfer. The prevailing mechanism is primarily dependent on the structure of the substrate. With carboxylic acids the one-electron oxidation occurs exclusively, leading to the loss of the carboxyl group and to formation of the alkyl radical. For alcohols both alkoxy radicals and hydrogen-abstraction α-carbon radicals were spin trapped. The alkoxy radicals were generated by the electron transfer mechanism. Finally pyrimidine bases such as thymine and cytosine yielded C(5)-centered radicals which could also be explained by an electron transfer mechanism. These observations are of interest because of the recently observed skin tumor-promoting activity of dibenzoyl peroxide. © 1982.
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