Hooker reaction

The Hooker reaction is an oxidative rearrangement reaction, discovered by Stanley C. Hooker in 1936, in which 2-hydroxy-3-alkyl-1,4-naphthoquinones are treated with an aqueous solution of potassium hydroxide and potassium permanganate to shorten the C3 alkyl side chain by one carbon atom (which bubbles out of solution as carbon dioxide). [1][2]

Mechanistically oxidation causes ring-cleavage at the alkene group, extrusion of carbon dioxide in decarboxylation with subsequent ring-closure.

References

  1. ^ On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate Samuel C. Hooker J. Am. Chem. Soc. 1936; 58(7); 1174–79. doi:10.1021/ja01298a030
  2. ^ On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate. Part II. Compounds with Unsaturated Side Chains Samuel C. Hooker and Al Steyermark J. Am. Chem. Soc. 1936; 58(7); pp. 1179–81; doi:10.1021/ja01298a031
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