Hydroxylation of nitrated naphthalenes with KO2/crown ether |
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| Authors: | Fukuhara K Hara Y Nakanishi I Miyata N |
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| Institution: | Division of Organic Chemistry, National Institute of Health Sciences, Tokyo, Japan. fukuhara@nihs.go.jp |
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| 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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