Abstract
A new approach has been proposed for the synthesis of keto acids via ozonolytic cleavage of 1-alkylcycloalkenes in a mixture of methylene chloride and acetic acid, followed by oxidation of peroxide ozonolysis products with 30% H2O2–SeO2.
REFERENCES
Gauptman, Z., Grefe, Yu., and Remane, Kh., Organicheskaya khimiya (Organic Chemistry), Moscow: Khimiya. 1979.
Ishmuratova, N.M., Ishmuratov, G.Yu., Yakovleva, M.P., Tambovtsev, K.A., Ismagilova, A.F., and Tolstikov, G.A., Matochnoe veshchestvo medonosnykh pchel: svoistva, sintez, primenenie v pchelovodstve i shmelevodstve (The Mother Substance of Honey Bees: Properties, Synthesis, and Application in Beekeeping and Bumblebee Breeding), Moscow: Nauka, 2015.
Ishmuratov, G.Yu., Yakovleva, M.P., Ishmuratova, N.M., Tolstikov, A.G., and Tolstikov, G.A., Monoterpenoidy v khimii opticheski aktivnykh feromonov nasekomykh (Monoterpenoids in the Chemistry of Optically Active Insect Pheromones), Moscow: Nauka, 2012.
Macaev, F.Z. and Malkov, A.V., Tetrahedron, 2006, vol. 62, p. 9. https://doi.org/10.1016/j.tet.2005.09.001
Myasoedova, Yu.V., Nazarov, I.S., and Ishmuratov, G.Yu., Russ. J. Org. Chem., 2019, vol. 55, p. 47. https://doi.org/10.1134/S107042801901007X
Bonjouklian, R., Cohen, J.D., Gruber, J.M., Johnson, D.W., Jungheim, L.N., Kroin, J.S., Lander, P.A., Lin, H.-S., Lohman, M.C., Muehl, B.S., Norman, B.H., Patel, V.F., Richett, M.E., Thrasher, K.J., Vepachedu, S., Wang, Q., White, W.T., Xie, Y., York, J.S., and Parkhurst, B.L., Int. Patent Appl. Pub. no. WO2001046199A1, 2001.
Naves, Y.-R. and Grampoloff, A.-V., Helv. Chim. Acta, 1961, vol. 44, p. 637. https://doi.org/10.1002/hlca.19610440304
Gajcy, K., Pękala, J., Frąckowiak-Wojtasek, B., Librowski, T., and Lochyński, S., Tetrahedron: Asymmetry, 2010, vol. 21, p. 2015. https://doi.org/10.1016/j.tetasy.2010.06.026
Yi, T., Shi, Z.-D., Qin, D.-G., Zhang, Y.-F., Wu, Y.-K., Li, Y., and Wu, Y.-L., Acta Chim. Sin., 2000, vol. 58, p. 448.
Latypova, L.R., Salikhov, Sh.M., Legostaeva, Yu.V., Khusnitdinov, R.N., Ishmuratov, G.Yu., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2018, vol. 54, p. 1313. https://doi.org/10.1134/S1070428018090075
Barbier, M. and Hugel, M.F., Bull. Soc. Chim. Fr., 1961, p. 951.
Appel, R. and Wihler, H.-D., Chem. Ber., 1976, vol. 109, p. 3446. https://doi.org/10.1002/cber.19761091023
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.
Birch, A.J., Mani, N.S., and Rao, G.S.R.S., J. Chem. Soc., Perkin Trans. 1, 1990, p. 1423. https://doi.org/10.1039/p19900001423
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. https://doi.org/10.1134/S1070428014080016
Ishmuratov, G.Yu., Yakovleva, M.P., Ganieva, V.A., Muslukhov, R.R., and Tolstikov, G.A., Chem. Nat. Compd., 2005, vol. 41, p. 41. https://doi.org/10.1007/s10600-005-0070-6
Gößnitzer, E., Punkenhofer, A., Amon, A., and Favre, B., Eur. J. Pharm. Sci., 2003, vol. 19, p. 151. https://doi.org/10.1016/s0928-0987(03)00086-1
Funding
This study was performed under financial support by the Russian Academy of Sciences, program “Fundamental Principles of Chemistry,” section no. 8: “Chemo-, Regio-, and Stereoselective Transformations of Terpenoids, Steroids, and Lipids in the Target-Oriented Synthesis of Low-Molecular-Weight Bioregulators” (state registry no. AAAA-A17117011910023-2, 2017) using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Russian Academy of Sciences) and Agidel joint center (Ufa Federal Research Center, Russian Academy of Sciences).
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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 107–110 https://doi.org/10.31857/S0514749222010128.
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Myasoedova, Y.V., Denisova, K.S., Yakovleva, M.P. et al. New Ozonolytic Synthesis of Keto Acids from 1-Alkylcycloalkenes. Russ J Org Chem 58, 163–166 (2022). https://doi.org/10.1134/S1070428022010237
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DOI: https://doi.org/10.1134/S1070428022010237