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Transformation of peroxide products of (S)-(-)-limonene ozonolysis in the system HCl-methanol

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Abstract

Peroxide products of partial ozonolysis of (S)-(-)-limonene (ee 50%) in cyclohexane-methanol at 2–4°C were treated with a solution of HCl in methanol, which led to the formation of a 4: 1 mixture of methyl [(1S)-2,4-dimethoxy-2,4-dimethylcyclohexyl]acetate and [(1S)-2,4-dimethoxy-2,4-dimethylcyclohexyl]acetaldehyde, each being represented by a single pair of diastereoisomers at a ratio of 3: 1.

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References

  1. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., Nasibullina, G.V., Muslukhov, R.R., Kazakov, D.V., and Tolstikov, G.A., Russ. J. Org. Chem., 2012, vol. 48, p. 18.

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  2. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., and Tolstikov, G.A., Russ. J. Org. Chem., 2014, vol. 50, p. 1075.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    G. Yu. Ishmuratov, Yu. V. Legostaeva, L. R. Garifullina, L. P. Botsman & R. R. Muslukhov

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    G. A. Tolstikov

Authors
  1. G. Yu. Ishmuratov
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  2. Yu. V. Legostaeva
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  3. L. R. Garifullina
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  4. L. P. Botsman
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  5. R. R. Muslukhov
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  6. G. A. Tolstikov
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Corresponding author

Correspondence to G. Yu. Ishmuratov.

Additional information

Original Russian Text © G.Yu. Ishmuratov, Yu.V. Legostaeva, L.R. Garifullina, L.P. Botsman, R.R. Muslukhov, G.A. Tolstikov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 12, pp. 1765–1767.

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Ishmuratov, G.Y., Legostaeva, Y.V., Garifullina, L.R. et al. Transformation of peroxide products of (S)-(-)-limonene ozonolysis in the system HCl-methanol. Russ J Org Chem 50, 1746–1748 (2014). https://doi.org/10.1134/S1070428014120045

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  • DOI: https://doi.org/10.1134/S1070428014120045

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