Hydroxylation of Nitrated Naphthalenes with KO₂/Crown Ether

抄録

Superoxide radical anion (O^·-₂), generated by KO₂/crown ether, is effective for hydroxylation of nitronaphthalenes. When mono- and di-nitronaphthalenes are treated with KO₂/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 reduction potential of nitronaphthalenes.