Issue 8, 2013

On the decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid – oxidation of the enol intermediate by triplet oxygen

Abstract

The formation of 2-methyl-1-tetralone from the metal-free and base-free decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid involves 2-methyl-3,4-dihydro-1-naphthol as an intermediate. The reaction of this enol with atmospheric oxygen leads to 2-hydroperoxy-2-methyl-1-tetralone. The oxidation mechanism is confirmed by quantum chemical calculations at the (U)B3LYP/6-31G(d) level of theory.

Graphical abstract: On the decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid – oxidation of the enol intermediate by triplet oxygen

Supplementary files

Additions and corrections

Article information

Article type
Letter
Submitted
01 May 2013
Accepted
13 May 2013
First published
14 May 2013

New J. Chem., 2013,37, 2245-2249

On the decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid – oxidation of the enol intermediate by triplet oxygen

A. Riahi, J. Muzart, M. Abe and N. Hoffmann, New J. Chem., 2013, 37, 2245 DOI: 10.1039/C3NJ00457K

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