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Decomposition of ozonolysis peroxide products of (+)-α- and (+)-β-pinenes in methanol by Fe(III) salts

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The reaction of ozonolysis peroxide products of (+)-α and (+)-β-pinenes with Fe(III) salts in MeOH was studied. It was found that decomposition of methoxyhydroperoxides obtained via ozonolysis of (+)-β-pinene using FeCl3⋅6H2O occurred at room temperature with formation of nopinone and its 3-chloro derivative; under reflux, nopinone and p-isopropylphenol. Replacing FeCl3⋅6H2O by Fe(NO3)3⋅9H2O produced the single product nopinone. Decomposition of peroxide compounds obtained via ozonolysis of (+)-α-pinene using FeCl3⋅6H2O gave a mixture of (1S,3S)-3-acetyl-2,2-dimethyl-1-(2,2-dimethoxyethyl)cyclobutane and [(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetate.

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Acknowledgment

The work was supported financially by the Ministry of Education and Science (State Contract No. 14.740.11.0367).

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, Prosp. Oktyabrya, 71, Russia

    E. V. Salimova, V. G. Kasradze & L. V. Spirikhin

  2. Bashkir State University, 450074, Ufa, Ul. Mingazheva, 100, Russia

    L. R. Garifullina & O. S. Kukovinets

Authors
  1. L. R. Garifullina
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  2. E. V. Salimova
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  3. V. G. Kasradze
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  4. L. V. Spirikhin
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  5. O. S. Kukovinets
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Correspondence to E. V. Salimova.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2012, pp. 707–709.

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Garifullina, L.R., Salimova, E.V., Kasradze, V.G. et al. Decomposition of ozonolysis peroxide products of (+)-α- and (+)-β-pinenes in methanol by Fe(III) salts. Chem Nat Compd 48, 791–793 (2012). https://doi.org/10.1007/s10600-012-0384-0

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  • DOI: https://doi.org/10.1007/s10600-012-0384-0

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