Réaction de Hooker

Réaction de Hooker

La réaction de Hooker (1936) est une réaction qui permet de réduire groupe méthylène par groupe méthylène une chaine alkyle de certaines naphtoquinones par l'action oxydante du permanganate de potassium[1],[2]. Ce phénomène a été observé la première fois sur le lapachol, une substance présente dans l'arbre lapacho.

Réaction de Hooker sur la 2-hydroxy-3-(3-phénylpropyl)naphtalène-1,4-dione

L'oxydation provoque une rupture de cycle au niveau du groupe alcène et un rejet de dioxyde de carbone dû à une décarboxylation. Le cycle se referme ensuite.

Notes et références

  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); 1174-1179. 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 - 1181; DOI:10.1021/ja01298a031

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