Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen |
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Authors: | V. L. Novikov O. P. Shestak |
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Affiliation: | 1149. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159 prosp. 100 let Vladivostoku, 690022, Vladivostok, Russian Federation
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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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