Hydroxylation of nitrated naphthalenes with KO2/crown ether.
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.
Fukuhara
K
K
Division of Organic Chemistry, National Institute of Health Sciences, Tokyo, Japan. fukuhara@nihs.go.jp
Hara
Y
Y
Nakanishi
I
I
Miyata
N
N
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*
D004988:Ethers, Cyclic; D009281:Naphthalenes; D009566:Nitrates; D013481:Superoxides; C039316:potassium superoxide