On the decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid oxidation of the enol intermediate by triplet oxygenElectronic supplementary information (ESI) available: Experimental section with spectroscopic data and quantum chemical calculation data. See DOI: 10.1039/c3nj00457k

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...

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Bibliographic Details
Main Authors: Riahi, Abdelkhalek, Muzart, Jacques, Abe, Manabu, Hoffmann, Norbert
Format: Article
Language:English
Online Access:Get full text
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Summary: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. The metal-free and base-free decarboxylation of 2-methyl-1-tetralone-2-carboxylic acid involves an enol intermediate. Although spin-forbidden, this intermediate can be oxidized by addition of triplet oxygen as confirmed by quantum chemical calculations.
ISSN:1144-0546
1369-9261
DOI:10.1039/c3nj00457k