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Transformations of peroxide ozonolysis products of (1R,3R)-p-menth-4-en-3-ol in the presence of pyridine

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Abstract

Ozonolysis of (1R,3R)-p-menth-4-en-3-ol in methylene chloride or methanol in the presence of pyridine afforded a mixture of equimolar amounts of epimeric 1-[(2R,4S,6S)- and 1-[(2S,4S,6S)-6-hydroxy-4-methyltetrahydro-2H-pyran-2-yl]-2-methylpropan-1-ones. A probable reaction mechanism is discussed.

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References

  1. Ishmuratov, G.Yu., Latypova, E.R., Tukhvatshin, V.S., Smolnikov, A.A., Muslukhov, R.R., Ishmuratova, N.M., and Talipov, R.F., Khim. Prirodn. Soedin., 2012, p. 866.

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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, R. R. Muslukhov & A. S. Erastov

  2. Bashkir State University, ul. Zaki Validi 32, Ufa, 450076, Bashkortostan, Russia

    G. Yu. Ishmuratov, V. S. Tukhvatshin, A. V. Allagulova & A. V. Bannova

  3. 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. V. S. Tukhvatshin
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  3. R. R. Muslukhov
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  4. A. S. Erastov
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  5. A. V. Allagulova
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  6. A. V. Bannova
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  7. G. A. Tolstikov
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Corresponding author

Correspondence to G. A. Tolstikov.

Additional information

Original Russian Text © G.Yu. Ishmuratov, V.S. Tukhvatshin, R.R. Muslukhov, A.S. Erastov, A.V. Allagulova, A.V. Bannova, G.A. Tolstikov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 141–143.

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Ishmuratov, G.Y., Tukhvatshin, V.S., Muslukhov, R.R. et al. Transformations of peroxide ozonolysis products of (1R,3R)-p-menth-4-en-3-ol in the presence of pyridine. Russ J Org Chem 50, 133–136 (2014). https://doi.org/10.1134/S1070428014010242

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  • DOI: https://doi.org/10.1134/S1070428014010242

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