Skip to main content
SpringerLink
Log in

Synthesis and properties of heterocyclic β-nitronitrone: 1,2,2,5,5-pentamethyl-4-nitromethyl-3-imidazoline 3-oxide

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction of methyl nitrone, a derivative of 3-imidazoline 3-oxide, with methyl nitrate in the presence of PhLi results in β-nitronitrone. The tnteraction of the latter with electrophiles involves, as a rule, the methylene group. Nitrile oxide, which is an 3-imidazoline 3-oxide derivative, has been generated by thermolysis ofgem-nitrooxime. This easily dimerizes to furoxan or undergoes regioselective 1,3-dipolar cycloaddition with alkenes.

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. V. A. Reznikov and L. B. Volodarsky,Zh. Org. Khim., 1987,23, 214 [J. Org. Chem. USSR, 1987,23 (Engl. Transl.)].

    Google Scholar 

  2. V. A. Reznikov and L. B. Volodarsky,Khim. Geterotsikl. Soedin., 1987, 1101 [Chem. Heterocycl. Comp. USSR, 1987 (Engl. Transl.)].

  3. V. A. Reznikov, L. A. Vishnivetskaya, and L. B. Volodarsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 444 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 382 (Engl. Transl.)].

    Google Scholar 

  4. S. Rajappa,Tetrahedron, 1981,37, 1453.

    Google Scholar 

  5. V. V. Martin and L. B. Volodarsky,Izv. Akad. Nauk SSSR,Ser. Khim., 1979, 1336 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979,28 (Engl. Transl.)].

  6. V. A. Reznikov and L. B. Volodarsky,Khim. Geterotsikl. Soedin., 1991, 192 [Chem. Heterocycl. Compd. USSR, 1991 (Engl. Transl.)].

  7. L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova, inKhimiya furoksanov. Stroenie i sintez [Chemistry of Furoxans. Structure and Synthesis], Nauka, Moscow, 1981, 125 (in Russian).

    Google Scholar 

  8. V. V. Martin, L. A. Vishnivetskaya, I. A. Grigor'ev, S. A. Dikanov, and L. B. Volodarsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1616 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 1477 (Engl. Transl.)].

  9. G. Bianchi, C. De Micheli, and R. Gandolfi,Chemistry of Double-bonded Functional Groups, Suppl. A., Part 1, Ed. S. Patai, Interscience, New York, 1977, Ch. 6, 369.

    Google Scholar 

  10. V. V. Martin and L. B. Volodarsky,Khim. Geterotsikl. Soedin., 1979, 103 [Chem. Heterocycl. Compd. USSR, 1979 (Engl. Transl.)].

Download references

Author information

Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 ul Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

    V. A. Reznikov, L. A. Vishnivetskaya & L. B. Volodarsky

Authors
  1. V. A. Reznikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. A. Vishnivetskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. B. Volodarsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 295–298, February, 1994.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Reznikov, V.A., Vishnivetskaya, L.A. & Volodarsky, L.B. Synthesis and properties of heterocyclic β-nitronitrone: 1,2,2,5,5-pentamethyl-4-nitromethyl-3-imidazoline 3-oxide. Russ Chem Bull 43, 275–278 (1994). https://doi.org/10.1007/BF00695828

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00695828

Key words

Search

Navigation