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Chemical & pharmaceutical bulletin

Hydroxylation of nitrated naphthalenes with KO2/crown ether.


PMID 11045464

Abstract

Superoxide radical anion (O2*-), 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.

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