Direct evidence on the mechanism of the oxidation of 2,3-dimethylindole by inorganic peroxo anions

doi:10.1021/JO00078A027

Paper

Direct evidence on the mechanism of the oxidation of 2,3-dimethylindole by inorganic peroxo anions

Published Dec 1, 1993 · M. Balón, M. Muñoz, P. Guardado

Journal of Organic Chemistry

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Abstract

The mechanisms of the 2,3-dimethylindole (1) oxidation to 3-methylindole-2-carbaldehyde (3) by peroxodisulfate and peroxomonosulfate anions have been investigated in H 2 SO 4 /20% v/v methanol-water solutions. Because indolenines have been postulated as intermediates in the oxidation of some indole derivatives, we have also analyzed the reactivity of 3-hydroxy-2,3-dimethyl-3H-indole (2a) with both peroxo anions. From these and previous studies, it is concluded that the reactions proceed in three steps: electrophilic attack of the peroxidic bond at the C-3 atom of indole to form the indolenine intermediate, a second peroxo anion attack on the enamine tautomer of this intermediate followed by hydrolysis to give 3-methylindole-2-carbaldehyde (3)

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Key takeawayThe oxidation of 2,3-dimethylindole to 3-methylindole-2-carbaldehyde occurs in three steps: electrophilic attack on the peroxidic bond, peroxo anion attack on the enamine tautomer, and hydrolysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Direct evidence on the mechanism of the oxidation of 2,3-dimethylindole by inorganic peroxo anions

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References

Citations

Kinetics of Carvedilol Oxidation by Peroxodisulfate

Carvedilol oxidation by Peroxodisulfate in 40% methanol-water leads to the formation of carbazole 1,4 quinone, a stable indolic beta blocker.

A Kinetic Study on the Oxidation of Indole by Peroxomonosulphate in Acetonitrile Solvent

The oxidation of indole by peroxomonosulphate in acetonitrile solvent follows a total second order, first order reaction, with no polymerization and a nonradical pathway.

Kinetics of Pindolol Oxidation by Peroxodisulfate

The oxidation of pindolol by peroxodisulfate occurs in the pH range 0 to 4, with oxipindolol formed at low acid concentration and dioxipindolol at high acid concentration.

A kinetic and mechanistic study on the oxidation of indole‐3‐acetic acid by peroxodisulfate

The oxidation of indole-3-acetic acid by peroxodisulfate in aqueous acetic acid medium involves a nonradical mechanism, with a lower reactivity than peroxomonosulfate.

Kinetics and Mechanism of meso-Tetraphenylporphyrin Iron(III) Chloride Catalysed Oxidation of Indole-3-Acetic Acid by Peroxomonosulphate

Meso-tetraphenylporphyrin iron(III) chloride catalyzes the oxidation of indole-3-acetic acid by peroxomonosulphate, with significant catalytic activity observed in the presence of TPP.