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Ozonolytic Transformation of (S)-(–)-Limonene in HCl–Isopropanol

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Chemistry of Natural Compounds Aims and scope

Partial ozonolysis of (S)-(–)-limonene (ee 50%) in cyclohexane:isopropanol at 2–4°C formed the 1,2,4-trioxolane as a mixture of diastereomers in a 3:2 ratio. A solution of HCl in i-PrOH acted as a cleaving agent during decomposition of the peroxides and a cyclizing agent during formation of the diastereomeric 1,2,4-substituted cyclohexanes.

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  1. V. V. Plemenkov, Introduction to the Chemistry of Natural Compounds [in Russian], Kazan, 2001, 378 pp.

  2. G. Yu. Ishmuratov, Yu. V. Legostaeva, L. P. Botsman, G. V. Nasibullina, R. R. Muslukhov, D. V. Kazakov, and G. A. Tolstikov, Zh. Org. Khim., 48, 26 (2012).

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Correspondence to G. Yu. Ishmuratov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2015, pp. 63–65.

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Ishmuratov, G.Y., Legostaeva, Y.V., Garifullina, L.R. et al. Ozonolytic Transformation of (S)-(–)-Limonene in HCl–Isopropanol. Chem Nat Compd 51, 71–73 (2015).

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