Skip to main content
SpringerLink
Log in

Baeyer–Villiger Oxidation of Diastereomeric Michael Adducts of Levoglucosenone into Dilactones

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

Abstract

The oxidation of diastereomeric Michael adducts of levoglucosenone and cyclohexanone with 5 equiv of H2O2 in isopropanol at 60°C results in selective formation of a γ-lactone. The reaction with 50 equiv of H2O2 under the same conditions gave a 6-ketononano-9-lactone annulated to the γ-lactone ring. The keto group in the latter reacts with tosylhydrazine to form a hydrazone, unlike what is the case with 6-ketononano-9-lactones annulated to the pyran ring.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Khalilova, Yu.A., Spirikhin, L.V., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2014, vol. 50, p. 125. https://doi.org/10.1134/S1070428014010217

    Article  CAS  Google Scholar 

  2. Galimova, Yu.S., Tagirov, A.R., Faizullina, L.Kh., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2017, vol. 53, p. 374. https://doi.org/10.1134/S1070428017030113

    Article  CAS  Google Scholar 

  3. Tagirov, A.R., Biktagirov, I.M., Galimova, Yu.S., Faizullina, L.Kh., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2015, vol. 51, p. 569. https://doi.org/10.1134/S1070428015040181

    Article  CAS  Google Scholar 

  4. Khalilova, Yu.A., Spirikhin, L.V., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2014, vol. 50, p. 125. https://doi.org/10.1134/S1070428014010229

    Article  CAS  Google Scholar 

  5. Tagirov, A.R., Faizullina, L.Kh., Salikhov, Sh.M., and Valeev, F.A., Butlerov. Soobshch., 2014, vol. 39, p. 48.

    Google Scholar 

  6. Faizullina, L.Kh., Khalilova, Y.A., Salikhov, Sh.M., and Valeev, F.A., Chem. Heterocycl. Compd., 2018, vol. 54, p. 598. https://doi.org/10.1007/s10593-018-2314-y

    Article  CAS  Google Scholar 

  7. Masumoto, K., Takashi, E., Koshi, K., Koji, O., Hiroshi, K., and Hajime, M., Bull. Chem. Soc. Jpn., 1995, vol. 68, p. 670. https://doi.org/10.1246/bcsj.68.670

    Article  Google Scholar 

  8. Valeev, F.A., Gaisina, I.N., Sagitdinova, Kh.F., Shitikova, O.V., and Miftakhov, M.S., Russ. J. Org. Chem., 1996, vol. 32, p. 1319.

    Google Scholar 

  9. Valeev, F.A., Gaisina, I.N., and Miftakhov, M.S., Russ.Chem. Bull., 1996, vol. 45, p. 1942. https://doi.org/10.1007/BF01457782

    Article  Google Scholar 

  10. Flourat, A.L., Peru, A.A.M., Teixeira, A.R.S., Brunissen, F., and Allais, F., Green Chem., 2015, vol. 17, p. 404. https://doi.org/10.1039/C4GC01231C

    Article  CAS  Google Scholar 

  11. Davydova, A.N., Pershin, A.A., Sharipov, B.T., and Valeev, F.A., Mendeleev Commun., 2015, vol. 25, p. 271. https://doi.org/10.1016/j.mencom.2015.07.013

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

Analyses were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The work was performed according to the State order (contract no. АААА-А17-117011910022-5) and financially supported by the Russian Foundation for Basic Research (project no. 17-43-020166-r_а).

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Researcher Centre, RAS, 450054, Ufa, Russia

    L. Kh. Faizullina, Yu. S. Galimova & F. A. Valeev

Authors
  1. L. Kh. Faizullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. S. Galimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. A. Valeev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. Kh. Faizullina.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Faizullina, L.K., Galimova, Y.S. & Valeev, F.A. Baeyer–Villiger Oxidation of Diastereomeric Michael Adducts of Levoglucosenone into Dilactones. Russ J Org Chem 56, 197–201 (2020). https://doi.org/10.1134/S1070428020020037

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020020037

Keywords:

Search

Navigation