Skip to main content
SpringerLink
Log in

Specificity of the Reaction of Tetranitromethane with Alkenes in Nitromethane

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

Abstract

Reactions of tetranitromethane with a number of di- and trisubstituted olefins in nitromethane were studied. Vinylcyclopropanes and phenylcycloalkenes reacted with tetranitromethane in an unexpected fashion, leading to formation of alkyltrinitromethanes and vicinal nitro alcohols.

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. Tartakovskii, V.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1984, p. 165.

  2. Altukhov, K.V. and Perekalin, V.V., Usp. Khim., 1976, vol. 45, p. 2050.

    CAS  Google Scholar 

  3. Novikov, S.S., Shvekhgeimer, G.A., Sevost'yanova, V.V, and Shlyapochnikov, V.A., Khimiya alifaticheskikh i alitsiklicheskikh nitrosoedinenii (Chemistry of Aliphatic and Alicyclic Nitro Compounds), Moscow: Khimiya, 1974, p. 416.

    Google Scholar 

  4. Ratsino, E.V., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1973, vol. 9, p. 58.

    CAS  Google Scholar 

  5. Averina, E.B., Ivanova, O.A., Grishin, Yu.K., Kuznetsova, T.S., and Zefirov, N.S., Russ. J. Org. Chem., 2000, vol. 36, p. 1562.

    CAS  Google Scholar 

  6. Ivanova, O.A., Averina, E.B., Grishin, Yu.K., Kuznetsova, T.S., and Zefirov, N.S., Dokl. Ross. Akad. Nauk, 2002, vol. 382, p. 71.

    Google Scholar 

  7. Budynina, E.M., Averina, E.B., Ivanova, O.A., Grishin, Yu.K., Kuznetsova, T.S., and Zefirov, N.S., Dokl. Ross. Akad. Nauk, 2002, vol. 382, p. 210.

    Google Scholar 

  8. Averina, E.B., Budynina, E.M., Ivanova, O.A., Grishin, Yu.K., Gerdov, S.M., Kuznetsova, T.S., and Zefirov, N.S., Russ. J. Org. Chem., 2004, vol. 40, p. 162.

    CAS  Google Scholar 

  9. Yanovskaya, L.A., Dombrovskii, V.A., and Khusid, A.Kh., Tsiklopropany s funktsional'nymi gruppami (Functionally Substituted Cyclopropanes), Moscow: Nauka, 1980, p. 221.

    Google Scholar 

  10. Wiberg, K.B., and Ashe, A.J., III, J. Am. Chem. Soc., 1968, vol. 90, p. 63.

    CAS  Google Scholar 

  11. Mathew, L., Varghese, B., and Sankararaman, S., J. Chem. Soc., Perkin Trans. 2, 1993, p. 2399; Eberson, L., Hartshorn, M.P., and Persson, O., Acta Chem. Scand., 1998, vol. 52, p. 450.

  12. Buevich, V.A., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1971, vol. 7, p. 1380.

    CAS  Google Scholar 

  13. Ballini, R., Bartoli, G., Gariboldi, P.V., Marcantoni, E., and Petrini, M., J. Org. Chem., 1993, vol. 58, p. 3368.

    Article  CAS  Google Scholar 

  14. Buevich, V.A, Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1970, vol. 6, p. 658; Ratsino, E.V., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1972, vol. 8, p. 523; Penczek, S., Jagur-Grodzinski, J., and Szwarc, M., J. Am. Chem. Soc., 1968, vol. 90, p. 2174.

    CAS  Google Scholar 

  15. Organic Syntheses, Horning, E.C., Ed., New York: Wiley, 1955, collect. vol. 3, p. 803.

    Google Scholar 

  16. Crawford, R.J. and Cameron, D.M., Can. J. Chem., 1967, vol. 45, p. 691.

    CAS  Google Scholar 

  17. Zefirov, N.S., Kuznetsova, T.S., Budyka, M.I., and Koz'min, A.S., Zh. Org. Khim., 1978, vol. 14, p. 2006.

    Google Scholar 

  18. Sheldrick, G.M., SHELXTL V5.10, Madison, WI-53719, USA: Bruker AXS Inc., 1997.

    Google Scholar 

  19. Govindachari, T.R., Nagarajan, K., Pai, B.R., and Arumugan, N., J. Chem. Soc., 1956, p. 4280.

  20. Buevich, V.A., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1967, vol. 3, p. 2248.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob'evy gory 1, Moscow, 119899, Russia

    O. A. Ivanova, E. B. Averina, E. M. Budynina, A. A. Korlyukov, M. Yu. Antipin, T. S. Kuznetsova & N. S. Zefirov

Authors
  1. O. A. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. B. Averina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. M. Budynina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Korlyukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Yu. Antipin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. S. Kuznetsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. S. Zefirov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 9, 2005, pp. 1292–1297.

Original Russian Text Copyright © 2005 by Ivanova, Averina, Budynina, Korlyukov, Antipin, Kuznetsova, Zefirov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivanova, O.A., Averina, E.B., Budynina, E.M. et al. Specificity of the Reaction of Tetranitromethane with Alkenes in Nitromethane. Russ J Org Chem 41, 1265–1270 (2005). https://doi.org/10.1007/s11178-005-0333-5

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0333-5

Keywords

Search

Navigation