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

摘要

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.