Skip to main content
Log in

New Ozonolytic Synthesis of Keto Acids from 1-Alkylcycloalkenes

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme

REFERENCES

  1. Gauptman, Z., Grefe, Yu., and Remane, Kh., Orga­nicheskaya khimiya (Organic Chemistry), Moscow: Khimiya. 1979.

  2. 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.

  3. 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.

  4. Macaev, F.Z. and Malkov, A.V., Tetrahedron, 2006, vol. 62, p. 9. https://doi.org/10.1016/j.tet.2005.09.001

    Article  CAS  Google Scholar 

  5. 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

    Article  CAS  Google Scholar 

  6. 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.

  7. Naves, Y.-R. and Grampoloff, A.-V., Helv. Chim. Acta, 1961, vol. 44, p. 637. https://doi.org/10.1002/hlca.19610440304

    Article  CAS  Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. 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.

    CAS  Google Scholar 

  10. 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

    Article  CAS  Google Scholar 

  11. Barbier, M. and Hugel, M.F., Bull. Soc. Chim. Fr., 1961, p. 951.

  12. Appel, R. and Wihler, H.-D., Chem. Ber., 1976, vol. 109, p. 3446. https://doi.org/10.1002/cber.19761091023

    Article  CAS  Google Scholar 

  13. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

  14. 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

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  PubMed  Google Scholar 

Download references

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).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. P. Yakovleva.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 107–110 https://doi.org/10.31857/S0514749222010128.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022010237

Keywords:

Navigation