Skip to main content
SpringerLink
Log in

Aluminum oxide-induced gas-phase ring-opening in methyl substituted gem-difluorocyclopropanes, leading to 2-fluorobuta-1,3-dienes and vinylacetylenes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A gas-phase pyrolysis of methyl-substituted gem-difluorocyclopropanes in a flow-tube reactor in the presence of Al2O3 at 185—250 °C gives 2-fluorobuta-1,3-dienes and vinylacetylenes.

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. H. Jendralla, Cyclopropyl to allyl rearrengement, in Methods of Organic Chemistry (Houben-Weyl), Ed. A. de Meijere, Thieme, Stuttgart, 1997, Vol. E17c, 2313

    Google Scholar 

  2. R. R. Kostikov, A. P. Molchanov, H. Hopf, Top. Curr. Chem., 1990, 155, 41

    Article  CAS  Google Scholar 

  3. M. Fedorynski, Chem. Rev., 2003, 103, 1099

    Article  CAS  Google Scholar 

  4. W. R. Dolbier, Jr., M. A. Battiste, Chem. Rev., 2003, 103, 1071

    Article  CAS  Google Scholar 

  5. R. Bartlet, Y. Quang, Bull. Soc. Chim. Fr., 1969, 3729

    Google Scholar 

  6. M. Schlosser, Tetrahedron, 1978, 34, 3.

    Article  CAS  Google Scholar 

  7. R. Fields, R. N. Haszeldine, D. Peter, J. Chem.Soc. (C), 1969, 165–172

    Google Scholar 

  8. K. A. Holbrook, K. A. W. Parry, J. Chem. Soc. (B), 1970, 1019.

    Google Scholar 

  9. N. V. Volchkov, M. A. Novikov, M. B. Lipkind, O. M. Nefedov, Mendeleev Commun., 2013, 19

    Google Scholar 

  10. M. A. Novikov, N. V. Volchkov, M. B. Lipkind, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 71 [Izv. Akad. Nauk, Ser. Khim., 2013, 71].

    Article  CAS  Google Scholar 

  11. G. C. Robinson, J. Org. Chem., 1968, 33, 607

    Article  CAS  Google Scholar 

  12. M. S. Baird, B. S. Mahli, L. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1990, 1881

    Google Scholar 

  13. R. P. Clifford, K. A. Holbrook, J. Chem. Soc., Perkin Trans. 2, 1972, 1972.

    Google Scholar 

  14. N. V. Volchkov, M. B. Lipkind, A. V. Zabolotskikh, A. V. Ignatenko, O. M. Nefedov, Mendeleev Commun., 2006, 153.

    Google Scholar 

  15. P. Weyerstahl, D. Klamann, C. Finger, M. Fligge, F. Nerdel, J. Buddrus, Chem. Ber., 1968, 101, 1303.

    Article  CAS  Google Scholar 

  16. E. V. Guseva, N. V. Volchkov, Yu. V. Tomilov, O. M. Nefedov, Eur. J. Org. Chem., 2004, 14, 3136.

    Article  Google Scholar 

  17. T. B. Patrick, J. Rogers, K. Gorrell, Org. Lett., 2002, 4, 3155.

    Article  CAS  Google Scholar 

  18. O. M. Nefedov, N. V. Volchkov, Mendeleev Commun., 2006, 121.

    Google Scholar 

  19. (a)_O. M. Nefedov, A. A. Ivashenko, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1968, 17, 445 [Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 446]

    Article  Google Scholar 

  20. O. M. Nefedov, A. A. Ivashenko, Bull. Acad. Sci. USSR, Div. Chem.Sci. (Engl. Transl.), 1968, 17, 1346 [Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 1417]

    Article  Google Scholar 

  21. N. V. Volchkov, A. V. Zabolotskikh, A. V. Ignatenko, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1990, 39, 1458 [Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1609]

    Article  Google Scholar 

  22. N. V. Volchkov, A. V. Zabolotskikh, M. B. Lipkind, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem.Sci. (Engl. Transl.), 1989, 38, 1782 [Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1935].

    Article  Google Scholar 

  23. W. E. Parham, R. R. Twelves, J. Org. Chem., 1957, 22, 730.

    Article  CAS  Google Scholar 

  24. M. Christl, M. Braun, H. Fischer, S. Groetsch, G. Muller, D. Leusser, S. Deuerlein, D. Stalke, M. Arnone, B. Engels, Eur. J. Org. Chem., 2006, 5045.

    Google Scholar 

  25. W. R. Dolbier, Jr., J. J. Keaffaber, C. R. Burkholder, H. Koroniac, J. Pradhan, Tetrahedron, 1992, 48, 9649.

    Article  CAS  Google Scholar 

  26. W. R. Dolbier, Jr., Acc. Chem. Res., 1981, 14, 195

    Article  CAS  Google Scholar 

  27. W. R. Dolbier, Jr., S. F. Sellers, J. Am. Soc. Chem., 1982, 104, 2494

    Article  CAS  Google Scholar 

  28. W. R. Dolbier, Jr., S. F. Sellers, J. Org. Chem., 1982, 47, 1

    Article  CAS  Google Scholar 

  29. J. C. Ferrero, E. A. R. De Staricco, E. H. Staricco. J. Phys. Chem., 1975, 79, 1242.

    Article  CAS  Google Scholar 

  30. W. R. Dolbier, Jr., H. O. Enoch, J. Am. Soc. Chem., 1977, 99, 4532–4533.

    Article  CAS  Google Scholar 

  31. J. M. Birchall, R. N. Haszeidine, D. W. Roberts, J. Chem. Soc., Chem. Commun., 1967, 287.

    Google Scholar 

  32. B. Atkinson, D. McKeagan. J. Chem. Soc., Chem. Commun., 1966, 287.

    Google Scholar 

  33. N. V. Volchkov, M. B. Lipkind, A. V. Zabolotskikh, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1990, 39, 211 [Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 228].

    Article  Google Scholar 

  34. N. V. Volchkov, M. B. Lipkind, A. V. Zabolotskikh, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 2250 [Izv. Akad. Nauk, Ser. Khim., 2014, 2250].

    Article  CAS  Google Scholar 

  35. I. V. Kozhernikov, Chem. Rev., 1998, 98, 171

    Article  Google Scholar 

  36. R. Mello, A. Alcalde-Aragones, M. E. Gonzalez-Nunez, Tetrahedron Lett., 2010, 51, 4281.

    Article  CAS  Google Scholar 

  37. M. Kamel, W. Kimpenhaus, J. Buddrus, Chem. Ber., 1976, 109, 2351.

    Article  CAS  Google Scholar 

  38. R. A. Mitsch, J. Am. Chem. Soc., 1965, 87, 758.

    Article  CAS  Google Scholar 

  39. M. L. Brewitz, J. Llaverid, A. Yada, A. Fürstner, Chemistry—A European J., 2013, 19, 4532.

    Article  CAS  Google Scholar 

  40. R. Vestin, A. Borg, T. Lindblom, Acta Chem. Scand., 1968, 22, 687.

    Article  CAS  Google Scholar 

  41. E. Defranq, T. Zesiger, R. Tabacchi. Helv. Chim. Acta, 1993, 76, 425.

    Article  CAS  Google Scholar 

  42. W. S. Trahanovsky, S. L. Emeis, J. Am. Chem. Soc., 1975, 97, 3773.

    Article  CAS  Google Scholar 

  43. R. Mello, A. Alcalde-Aragones, M. E. Gonzalez-Nunez, Tetrahedron Lett., 2010, 51, 4281.

    Article  CAS  Google Scholar 

  44. C. Delseth, T. T.-T. Nguyen, J.-P. Kintzinger, Helv. Chim. Acta., 1980, 63, 498.

    Article  CAS  Google Scholar 

  45. D. Derouet, L. Cauret, J.-C. Brosse, J. Org. Chem., 2001, 66, 3767.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    N. V. Volchkov, M. B. Lipkind, M. A. Novikov & O. M. Nefedov

Authors
  1. N. V. Volchkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. B. Lipkind
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. M. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. V. Volchkov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0658—0663, March, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Volchkov, N.V., Lipkind, M.B., Novikov, M.A. et al. Aluminum oxide-induced gas-phase ring-opening in methyl substituted gem-difluorocyclopropanes, leading to 2-fluorobuta-1,3-dienes and vinylacetylenes. Russ Chem Bull 64, 658–663 (2015). https://doi.org/10.1007/s11172-015-0914-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0914-6

Key words

Search

Navigation