Superoxide radical anion (O·-2), generated by KO 2/crown ether, is effective for hydroxylation of nitronaphthalenes. When mono-and di-nitronaphthalenes are treated with KO 2/crown ehter, hydroxylation results at the electron-deficient site caused by the electron withdrawing effect of the substituted nitro group. Kinetic experiments suggest that the hydroxylation proceeds by two different mechanisms dependent on the first one-electron ...
