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Oxidation of 1,3-Dioxacycloalkanes with Complexes of Potassium Chlorochromate and Chlorodiperoxochromate with 15-Crown-5, Catalyzed with 2,2,5,5-Tetramethyl- 4-phenyl-3-oxo-3λ5-imidazolin-1-yloxyl

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Abstract

2,2,5,5-Tetramethyl-4-phenyl-3-oxo-3λ5-imidazolin-1-yloxyl catalyzes oxidation of 2-isopropyl-1,3-dioxolane, 2-phenyl-1,3-dioxolane, 2-phenyl-4-chloromethyl-1,3-dioxolane, and 2-phenyl-1,3-dioxane with 15-crown-5 complexes of potassium chlorodiperoxochromate (KCrO5Cl·2C10H20O5) and potassium chlorochromate (KCrO3Cl·2C10H20O5). 2-Isopropyl-1,3-dioxolane is oxidized to the corresponding monoester in quantitative yield, and the 2-phenyl derivatives yield benzaldehyde. The spiro ketal, 2,2-pentamethylene-4-methyl-1,3-dioxane, is decomposed to cyclohexanone.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia

    Z. F. Akbalina, N. N. Kabal'nova, S. S. Zlotskii, I. A. Grigor'ev, S. A. Kotlyar, V. V. Shereshovets & G. A. Tolstikov

  2. Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia

    Z. F. Akbalina, N. N. Kabal'nova, S. S. Zlotskii, I. A. Grigor'ev, S. A. Kotlyar, V. V. Shereshovets & G. A. Tolstikov

  3. Reaktiv Research Institute of Low-Tonnage Chemical Products and Reagents, Ufa, Bashkortostan, Russia

    Z. F. Akbalina, N. N. Kabal'nova, S. S. Zlotskii, I. A. Grigor'ev, S. A. Kotlyar, V. V. Shereshovets & G. A. Tolstikov

  4. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine

    Z. F. Akbalina, N. N. Kabal'nova, S. S. Zlotskii, I. A. Grigor'ev, S. A. Kotlyar, V. V. Shereshovets & G. A. Tolstikov

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  1. Z. F. Akbalina
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  2. N. N. Kabal'nova
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  3. S. S. Zlotskii
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  4. I. A. Grigor'ev
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  5. S. A. Kotlyar
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  6. V. V. Shereshovets
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  7. G. A. Tolstikov
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Akbalina, Z.F., Kabal'nova, N.N., Zlotskii, S.S. et al. Oxidation of 1,3-Dioxacycloalkanes with Complexes of Potassium Chlorochromate and Chlorodiperoxochromate with 15-Crown-5, Catalyzed with 2,2,5,5-Tetramethyl- 4-phenyl-3-oxo-3λ5-imidazolin-1-yloxyl. Russian Journal of General Chemistry 72, 447–448 (2002). https://doi.org/10.1023/A:1015533921604

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  • DOI: https://doi.org/10.1023/A:1015533921604

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