Skip to main content
SpringerLink
Log in

Catalytic Reaction of substituted 1,3-oxathiolanes with diazocarbonyl compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of substituted 1,3-oxathiolanes with diazocarbonyl compounds in the presence of Cu(OTf)2 and Rh2(OAc)4 was studied. The reaction is accompanied by the insertion of an alkoxycarbonylmethylene fragment into the C–S bond of the oxathiolane ring and leads to the formation of heterocyclic and heteroaliphatic products.

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

Similar content being viewed by others

References

  1. Doyle, M. P.; McKervey, M. A.; Ye, T.; Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylide; Wiley: New York, 1998, p. 652.

    Google Scholar 

  2. Shapiro, E. A.; Dyatkin, A. B.; Nefedov, O. M. Russ. Chem. Rev.1993, 62, 447. [Usp. Khim.1993, 62, 485.]

  3. Clark, J. S.; Baxter, C. A.; Castro, J. L. Synthesis2005, 3398.

  4. Qu, J.-P.; Xu, Z.-H.; Zhou, J.; Cao, C.-L.; Sun, X.-L.; Dai, L.-X.; Tang, Y. Adv. Synth. Catal. 2009, 351, 308.

    Article  CAS  Google Scholar 

  5. Hodgson, D. M.; Angrish, D.; Erickson, S. P.; Kloesges, J.; Lee, C. H. Org. Lett.2008, 10, 5553.

    Article  CAS  Google Scholar 

  6. Marmsater, F. P.; West, F. G. J. Am. Chem. Soc.2001, 123, 5144.

    Article  CAS  Google Scholar 

  7. Yakura, T.; Muramatsu, W.; Uenishi, J. Chem. Pharm. Bull. 2005, 53, 989.

    Article  CAS  Google Scholar 

  8. Nitrogen, Oxygen and Sulfur Ylide Chemistry; Clark, J. S., Ed.; Oxford University Press: Oxford, 2002, p. 141.

  9. Yanovskaya, L. A.; Yufit, S. S.; Kucherov, V. F. Khimiya atsetalei [in Russian]; Moscow: Nauka, 1975.

    Google Scholar 

  10. Greenе, T. W.; Wuts, P. G. N. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991, 2nd ed., Vol. 4.

  11. Burdock, G. A. Fenaroli's Handbook of Flavor Ingredients; New York, 1995, 3th ed., Vol. 2.

  12. Ley, S. V.; Priepke, H. W. M. Angew. Chem. 1994, 106, 2412.

    Article  CAS  Google Scholar 

  13. Blickenstaff, R. T.; Brandstadter, S. M.; Foster, E.; Reddy, S.; Witt, R. Ind. Eng. Chem. Res. 1993, 32, 2455.

    Article  CAS  Google Scholar 

  14. Sarmiento-Sánchez, J. I.; Picos-Corrales, L. A. Chem. Heterocycl. Compd.2018, 54, 680. [Khim. Geterotsikl. Soedin.2018, 54, 680.]

  15. Petrov, D. A.; Sultanova, R. M.; Zlotskii, S. S.; Fatykhov, A. A. Dokl. Chem.2002, 385, 507. [Dokl. Akad. Nauk2002, 385, 507.]

  16. Sultanova, R. M.; Katashova, V. R.; Petrov, D. A.; Fatykhov, A. A.; Zlotsky, S. S.; Dokichev, V. A. Russ. Chem. Bull., Int. Ed.2001, 50, 865. [Izv. Akad. Nauk, Ser. Khim.2001, 828.]

  17. Khanova, M. D.; Sultanova, R. M.; Khursan, S. L.; Dokichev, V. A.; Tomilov, Yu. V. Russ. Chem. Bull., Int. Ed.2006, 55, 1464. [Izv. Akad. Nauk, Ser. Khim.2006, 1411.]

  18. Shaikhullina, G. N.; Sultanova, R. M.; Baikova, I. P.; Raskildina, G. Z.; Zlotsky, S. S. Russ. Chem. Bull., Int. Ed.2017, 66, 164. [Izv. Akad. Nauk, Ser. Khim.2017, 164.]

  19. Ozen, C.; Konuklar, F. A. S.; Tuzun, N. S. Organometallics2009, 28, 4964.

    Article  CAS  Google Scholar 

  20. Ioannou, M.; Porter, M. J.; Saez, F. Tetrahedron2005, 61, 43.

    Article  CAS  Google Scholar 

  21. Gordon, А.; Ford, R. Chemist's Companion [Russian translation]; Moscow: Mir, 1976.

    Google Scholar 

  22. Keil, B. Laboratoriumstechnik der organischen Chemie [Russian translation]; Moscow: Mir, 1966.

    Google Scholar 

  23. Rakhmankulov, D. L.; Zorin, V. V.; Latypova, F. N.; Musavirov, R. S.; Siraeva, I. N. Metody sinteza 1,3-digeteroanalogov tsikloalkanov [in Russian]; Ufa: Reaktiv, 1998.

    Google Scholar 

  24. Weygand-Hilgetag Preparative Organic Chemistry [Russian translation]; Moscow: Khimiya, 1968, p. 264.

Download references

This work was carried out in accordance with the topics of the State assignment to the Ufa Institute of Chemistry of the Ufa Federal Research Center of the Russian Academy of Sciences №№ АААА-А17-117011910025-6 and АААА-А17-117011910027-0.

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, 1 Kosmonavtov St., Ufa, 450062, Russia

    Gul’nur N. Sakhabutdinova, Gul’nara Z. Raskil’dina, Simon S. Zlotskii & Rimma M. Sultanova

  2. Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa, 450054, Russia

    Irina P. Baikova & Rimma M. Sultanova

Authors
  1. Gul’nur N. Sakhabutdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gul’nara Z. Raskil’dina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Irina P. Baikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Simon S. Zlotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rimma M. Sultanova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rimma M. Sultanova.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sakhabutdinova, G.N., Raskil’dina, G.Z., Baikova, I.P. et al. Catalytic Reaction of substituted 1,3-oxathiolanes with diazocarbonyl compounds. Chem Heterocycl Comp 55, 1222–1227 (2019). https://doi.org/10.1007/s10593-019-02605-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02605-3

Keywords

Search

Navigation