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Kinetics and mechanism of the oxidation of acetylacetone by permanganate ion

✍ Scribed by Miklós Jáky; János Szammer; Edit Simon-Trompler


Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
131 KB
Volume
38
Category
Article
ISSN
0538-8066

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✦ Synopsis


Abstract

The kinetics and mechanism of permanganate ion oxidation of acetylacetone (Acac) was studied in acidic and alkaline media. The rate constants for keto, enol, and enolate anions were determined and discussed. Delocalization of the π‐electrons of the double bond by conjugation results in a slower oxidation rate of enol than can be usually observed for unsaturated compounds. In the case of the keto form, the acid‐catalyzed nucleophilic attack of permanganate ion occurs on the carbonyl‐C atom. For enolate anion a mechanism with basis‐catalyzed electron abstraction is suggested. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 38: 444–450, 2006


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