title: Hydroxylation of nitrated naphthalenes with KO2/crown ether.
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.
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Tokyo, Japan. fukuhara@nihs.go.jp
authors.forename: K
authors.initials: K
authors.lastname: Fukuhara
authors.forename: Y
authors.initials: Y
authors.lastname: Hara
authors.forename: I
authors.initials: I
authors.lastname: Nakanishi
authors.forename: N
authors.initials: N
authors.lastname: Miyata
mesh_terms: D004988:Ethers, Cyclic / Q000737:chemistry*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry*; D009566:Nitrates / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013481:Superoxides / Q000737:chemistry*
chemical_list: D004988:Ethers, Cyclic; D009281:Naphthalenes; D009566:Nitrates; D013481:Superoxides; C039316:potassium superoxide