Skip to main content
SpringerLink
Log in

Addition of Alcohols to 4-Methylene-1,3-dioxolanes

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

Abstract

The addition of alcohols to 2-methylene-1,4-dioxaspiro[4.5]decane under the conditions of CF3CO2H catalysis occurs with the selective formation of the corresponding alkoxy derivatives. The conditions that ensure preparative isolation of target compounds in 63–94% yields have been determined, and relative activity of alcohols in the addition reaction at the exocyclic double bond of substrates has been determined.

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

REFERENCES

  1. Sudarsanam, P., Mallesham, B., Prasad, A.N., Reddy, P.S., and Reddy, B.M., Fuel Process. Technol., 2013, vol. 106, p. 539. https://doi.org/10.1016/j.fuproc.2012.09.025

    Article  CAS  Google Scholar 

  2. Kumar, K., Pathak, S., and Upadhyayula, S., Renew. Energy, 2021, vol. 167, p. 282. https://doi.org/10.1016/j.renene.2020.11.084

    Article  CAS  Google Scholar 

  3. Oparina, L.A., Vysotskaya, O.V., Stepanov, A.V., Gusarova, N.K., and Trofimov, B.A., Russ. J. Org. Chem., 2012, vol. 48, no. 9, p. 1162. https://doi.org/10.1134/S1070428012090023

    Article  CAS  Google Scholar 

  4. Moity, L., Benazzouz, A., Molinier, V., Nardello-Rataj, V., Elmkaddem, M.K., de Caro, P., Thiébaud-Roux, S., Gerbaud, V., Marione, P., and Aubry, J.-M., Green Chem., 2015, vol. 17, no. 3, p. 1779. https://doi.org/10.1039/C4GC02377C

    Article  CAS  Google Scholar 

  5. Raskil’dina, G.Z., Kuzmina, U.Sh., Dzhumaev, Sh.Sh., Borisova, Yu.G., Ishmetova, D.V., Vakhitova, Yu.V., and Zlotskii, S.S., Russ. Chem. Bull., 2021, vol. 70, no. 3, p. 475. https://doi.org/10.1007/s11172-021-3111-9

    Article  CAS  Google Scholar 

  6. Meng, S.-S., Liang, Y., Cao, K.-S., Zou, L., Lin, X.-B., Yang, H., Houk, K.N., and Zheng, W.-H., J. Am. Chem. Soc., 2014, vol. 136, no. 35, p. 12249. https://doi.org/10.1021/ja507332x

    Article  CAS  PubMed  Google Scholar 

  7. Johnsson, R., Ohlin, M., and Ellervik, U., J. Org. Chem., 2010, vol. 75, no. 23, p. 8003. https://doi.org/10.1021/jo101184d

    Article  CAS  PubMed  Google Scholar 

  8. Oparina, L.A., Kolyvanov, N.A., Ganina, A.A., and D’yachkova, S.G., Petrol. Chem., 2020, vol. 60, no. 1, p. 134. https://doi.org/10.1134/S0965544120010107

    Article  CAS  Google Scholar 

  9. Frauenrath, H. and Runsink, J., J. Org. Chem., 1988, vol. 53, no. 9, p. 1860. https://doi.org/10.1021/jo00244a004

    Article  CAS  Google Scholar 

  10. Orth, H., Angew. Chem., 1952, vol. 64, nos. 19–20, p. 544. https://doi.org/10.1002/ange.19520641908

    Article  CAS  Google Scholar 

  11. Brandsma, L., Synthesis of Acetylenes, Allenes and Cumulenes. Methods and Techniques, Amsterdam Elsevier, 2004, p. 123.

Download references

Funding

This study was performed in the scope of the State Task from the Ministry of Education and Science of Russia in the field of academic activity (no. FEUR–2022-0007 “Petrochemical reagents, oils, and materials for thermal power engineering”).

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450064, Ufa, Russia

    S. A. Sokov, Yu. G. Borisova, G. Z. Raskil’dina, S. S. Zlotsky & A. A. Golovanov

Authors
  1. S. A. Sokov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. G. Borisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. Z. Raskil’dina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. S. Zlotsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Golovanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. G. Borisova.

Ethics declarations

Authors declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokov, S.A., Borisova, Y.G., Raskil’dina, G.Z. et al. Addition of Alcohols to 4-Methylene-1,3-dioxolanes. Russ J Gen Chem 93, 2493–2497 (2023). https://doi.org/10.1134/S107036322310002X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036322310002X

Keywords:

Search

Navigation