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Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen

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Abstract

The major products of thermal (acetone, CaCl2 excess, reflux) and photochemical (acetone or CCl4, room temperature) oxidation of 2-acetylcyclopentanone with atmospheric oxygen are 2-acetyl-2-hydroxycyclopentanone, 2-acetyl-2-hydroxymethylcyclopentanone, 1,1′-diacetyl-1,1′-bicyclopentyl-2,2′-dione, 2-acetoxycyclopentanone, 5,6-dioxoheptanoic acid, glutaric acid, and glutaric anhydride. The formation of 2-acetyl-2-hydroxycyclopentanone is the first example of the direct α-hydroxylation of β-dicarbonyl compound under the conditions described.

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159 prosp. 100 let Vladivostoku, 690022, Vladivostok, Russian Federation

    V. L. Novikov & O. P. Shestak

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  1. V. L. Novikov
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  2. O. P. Shestak
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Correspondence to O. P. Shestak.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1092–1102, June, 2012.

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Novikov, V.L., Shestak, O.P. Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen. Russ Chem Bull 61, 1099–1110 (2012). https://doi.org/10.1007/s11172-012-0149-8

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  • DOI: https://doi.org/10.1007/s11172-012-0149-8

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