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Ozonolytic transformations of (S)-(−)-limonene

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Abstract

Partial ozonolysis of (S)-(−)-limonene in cyclohexane-methanol yields 1-methyl-4-(prop1-en-2-yl)-7,8,9-trioxabicyclo[4.2.1]nonane as a mixture of diastereoisomers at a ratio of 2: 3. Nitrogen-containing organic compounds (semicarbazide and hydroxylamine hydrochlorides) favor cyclization of intermediate ozonolysisreduction products, whereas the reduction with dimethyl sulfide, NaBH4, and NaBH(OAc)3 follows conventional pattern.

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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. P. Botsman, G. V. Nasibullina, R. R. Muslukhov, D. V. Kazakov & G. A. Tolstikov

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  1. G. Yu. Ishmuratov
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  2. Yu. V. Legostaeva
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  3. L. P. Botsman
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  4. G. V. Nasibullina
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  5. R. R. Muslukhov
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  6. D. V. Kazakov
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  7. G. A. Tolstikov
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Correspondence to G. Yu. Ishmuratov.

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Original Russian Text © G.Yu. Ishmuratov, Yu.V. Legostaeva, L.P. Botsman, G.V. Nasibullina, R.R. Muslukhov, D.V. Kazakov, G.A. Tolstikov, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 1, pp. 26–32.

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Ishmuratov, G.Y., Legostaeva, Y.V., Botsman, L.P. et al. Ozonolytic transformations of (S)-(−)-limonene. Russ J Org Chem 48, 18–24 (2012). https://doi.org/10.1134/S1070428012010034

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  • DOI: https://doi.org/10.1134/S1070428012010034

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