Skip to main content
SpringerLink
Log in

2-isoxazolines from arylcyclopropanes: I. Monoarylcyclopropanes in a reaction with nitrosyl chloride activated by sulfur(IV) oxide

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

Abstract

A reaction of monoarylcyclopropanes with nitrosyl chloride activated by sulfur (IV) oxide gave in good yields 5-arylisoxazolines. The reaction is of electrophilic character. A scheme of the reaction was suggested.

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. Kozikowski, A.P., Acc. Chem. Res., 1984, vol. 17, p. 410; Lipshuts, B.H., Chem. Res., 1986, vol. 86, p. 795; Lakhvich, F.A., Koroleva, E.V., and Akhrem, A.A., Khim. Geterotsikl. Soedin., 1989, p. 435; Koroleva, E.V. and Lakhvich, F.A., Usp. Khim., 1997, vol. 66, p. 31.

    Article  CAS  Google Scholar 

  2. Bondarenko, O.B., Gavrilova, A.Yu., Saginova, L.G., and Zyk, N.V., Zh. Org. Khim., 2003, vol. 39, p. 1084.

    Google Scholar 

  3. Bondarenko, O.B., Gavrilova, A.Yu., Saginova, L.G., Zyk, N.V., and Zefirov, N.S., Izv. Akad. Nauk, Ser. Khim., 2003, p. 741; Gazzaeva, R.A., Shabarov, Yu.S., and Saginova, L.G., Khim. Geterotsikl. Soedin., 1984, p. 309.

  4. Krayushkin, M.M., Kalik, M.A., Zav’yalova, V.K., Loktionov, A.A., and Bogdanov, V.S., Khim. Geterotsikl. Soedin., 1989, p. 1620.

  5. Rai, K.M.L. and Hassner, A., Indian J. Chem., 1997, vol. 36B, p. 242; Krayushkin, M.M., Loktionov, A.A., and Belen’kii, L.I., Khim. Geterotsikl. Soedin., 1988, p. 1034; Zyablikova, T.A., Buzykin, B.I., Dokuchaev, A.S., Sokolov, M.P., Gainullin, R.M., and Petrov, M.V., Abstracts of Papers, Fiz.-Khim. met. issl. strukturno-dinamicheskikh molekulyarnykh sistem. Vseross. soveshch. (All-Russian Meeting on Physicochemical Methods of Investigating of Structurally Flexible Molecular System), 1994, ch. 1, p. 94.

    CAS  Google Scholar 

  6. Park, K.P., Shiue, C.-Y., and Clapp, L.B., J. Org. Chem., 1970, vol. 35, p. 2065.

    Article  CAS  Google Scholar 

  7. Rheinboldt, R., Dewald, M., Jansen, F., and Schmitz-Dumont, O., Lieb. Ann., 1927, vol. 451, p. 161; Iwakura, Y., Uno, K., Shiraishi, S., and Hougu, T., Bull. Chem. Soc. Jpn., 1968, vol. 41, p. 2954; Torssell, K.B.G., Nitrile, Oxides, Nitrones, and, Nitronates in Organic Synthesis, New York: VCH, Publ, 1988.

    Google Scholar 

  8. Hegarty, A.F. and Mullane, M., J. Chem. Soc., Chem. Commun., 1984, p. 229.

  9. Mochalov, S.S., Kosynkin, D.V., Yudin, I.D., Zavodskikh, K.A., Shabarov, Yu.S., and Zefirov, N.S., Khim. Geterotsikl. Soedin., 1994, p. 472.

  10. Kost, A. and Ershov, V.V., Zh. Obshch. Khim., 1957, vol. 11, p. 3874.

    Google Scholar 

  11. Levina, R.Ya. and Gembitskii, P.A., Zh. Obshch. Khim., 1961, vol. 31, p. 3480.

    CAS  Google Scholar 

  12. Saginova, L.G., Bondarenko, O.B., Shabarov, Yu.S, and Gazzaeva, R.A., Zh. Org. Khim., 1984, vol. 20, p. 2124.

    CAS  Google Scholar 

  13. Shabarov, Yu.S., Potapov, V.K., and Levina, R.Ya., Zh. Obshch. Khim., 1964, vol. 34, p. 1964.

    Google Scholar 

  14. Applequist, D. and McKenzie, F., J. Org. Chem., 1976, vol. 41, p. 2264.

    Article  Google Scholar 

  15. Shabarov, Yu.S., Mochalov, S.S., Novokreshchennykh, V.D., Volkov, E.M., and Ermishkina, S.A., Zh. Org. Khim., 1975, vol. 11, p. 1907.

    CAS  Google Scholar 

  16. Veselovskaya, S.V., Saginova, L.G., and Shabarov, Yu.S., Zh. Org. Khim., 1987, vol. 23, p. 129.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Moscow State University, Moscow, 119899, Russia

    O. B. Bondarenko, A. Yu. Gavrilova, M. A. Kazantseva, L. G. Saginova & N. V. Zyk

  2. Moscow State Pedagogical University, Moscow, Russia

    V. N. Tikhanushkina & E. E. Nifant’ev

Authors
  1. O. B. Bondarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Gavrilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Kazantseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. N. Tikhanushkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. E. Nifant’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. G. Saginova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. V. Zyk
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. B. Bondarenko.

Additional information

Dedicated to Academician of the Russian Academy of Sciences N.S. Zefirov on occasion of his 70th anniversary

Original Russian Text © O.B. Bondarenko, A.Yu. Gavrilova, M.A. Kazantseva, V.N. Tikhanushkina, E.E. Nifant’ev, L.G. Saginova, N.V. Zyk, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 265–271.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bondarenko, O.B., Gavrilova, A.Y., Kazantseva, M.A. et al. 2-isoxazolines from arylcyclopropanes: I. Monoarylcyclopropanes in a reaction with nitrosyl chloride activated by sulfur(IV) oxide. Russ J Org Chem 42, 249–255 (2006). https://doi.org/10.1134/S1070428002120163

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428002120163

Keywords

Search

Navigation