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

New Journal of Chemistry Pub Date: 2013-05-14 DOI: 10.1039/C3NJ00457K

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
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