COOXIDATION OF ENONES DURING REACTION OF SUPEROXIDE WITH ACIDIC AROMATIC AMINES

Hiromasa TAKIZAWA; Tetsuo NAGANO; Masaaki HIROBE

doi:10.1248/cpb.39.1894

Hiromasa TAKIZAWA, Tetsuo NAGANO, Masaaki HIROBE

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Keywords: superoxide, Haber-Weiss reaction, hydrosyl radical, hydrogen peroxide, hydroperoxy anion, hydroperoxy radical, enone, oxidation

JOURNAL FREE ACCESS

1991 Volume 39 Issue 7 Pages 1894-1896

DOI https://doi.org/10.1248/cpb.39.1894

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Abstract

Enones can be epoxidized by O₂^-· in the presence of various compounds having an acidic >NH group. Cyclic voltammetry and ESR study show that O₂^-· was disproportionated into H₂O₂ and O₂ by these compounds. Furthermore, H₂O₂ was deprotonated by unreacted O₂^-· and HOO^- was formed, which is widely known to be the effective oxidant in the epoxidation of enones. This confirms the strong basicity of O₂^-· in aprotic media, and we propose an alternative scheme for the Haber-Weiss reaction in the absence of metal ions.

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