Tetrahedron letters

Nitration and hydroxylation of substituted phenols by peroxynitrite. Kinetic feature and an alternative mechanistic view

N Nonoyama, K Chiba, K Hisatome, H Suzuki…

Index: Nonoyama, Nobuaki; Chiba, Kazuhiko; Hisatome, Kaori; Suzuki, Hitomi; Shintani, Futoshi Tetrahedron Letters, 1999 , vol. 40, # 38 p. 6933 - 6937

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Citation Number: 40

Abstract

The reaction of peroxynitrite (ONOO−) with a series of para-substituted phenols has been examined in aqueous phosphate buffer and acetonitrile solutions. Major products were the corresponding 2-nitro derivative and the 4-substituted catechol. Kinetic study showed good correlation with Hammett σp+ parameters and reduction potentials, suggesting the possible one-electron transfer process involving the nitrosoniun ion (NO+) as initial electrophile ...