The Chemical Reactions of Superoxide with Halopyrimidines

Halopyrimidines such as 2-chloro-, 5-bromo, and 4,6-dichloro-5-nitropyrimidine undergo substitution reactions with superoxide anion radical (superoxide) to give the corresponding hydroxypyrimidines under suitable conditions. Parallel experiments employing hydroxide instead of superoxide strongly indicate that the reactivity of superoxide is comparable to that of the hydroxide in the reaction with halopyrimidines. The results seem to provide a piece of information in favor of the nucleophilic substitution rather than electron-transfer mechanism in the title reaction.