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.
Similar content being viewed by others
References
V. V. Plemenkov, Introduction to the Chemistry of Natural Compounds [in Russian], Kazan, 2001, 378 pp.
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).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2015, pp. 63–65.
Rights and permissions
About this article
Cite this article
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). https://doi.org/10.1007/s10600-015-1206-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-015-1206-y