Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Hydroxylation of Nitrated Naphthalenes with KO2/Crown Ether
Kiyoshi FUKUHARAYukie HARAIkuo NAKANISHINaoki MIYATA
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2000 Volume 48 Issue 10 Pages 1532-1535

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Abstract

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.

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