Skip to main content
SpringerLink
Log in

Nitroylides 6. Transfer of a nitromethylene fragment with the aid of iodonium nitroylides

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The ability of iodonium nitroylides to transfer a nitromethylene fragment to compounds containing a heteroatom with a lone pair has been demonstrated in the example of reactions with dimethyl sulfide, pyridine, and thiourea, making it possible to obtain various types of nitroylides, including the heretofore unknown pyridinium and diaminomethylenesulfonium dinitroylides.

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

Literature cited

  1. V. V. Semenov, S. A. Shevelev, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2640 (1976).

  2. V. V. Semenov, S. A. Shevelev, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2348 (1978).

  3. K. Wallenfels, K. Friedrich, J. Rieser, W. Ertel, and H. Thieme, Angew. Chem.,88, 311 (1976).

    Google Scholar 

  4. H. Matsuyama, H. Minato, and M. Kobayashi, Bull. Chem. Soc. Jpn.,46, 2845, 3158 (1973).

    Google Scholar 

  5. B. Ya. Karele and O. Ya. Neiland, Zh. Org. Khim.,4, 643 (1968);2, 1680 (1966).

    Google Scholar 

  6. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2032 (1976).

  7. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 1091 (1978).

  8. V. I. Slovetskii, L. I. Khmel'nitskii, O. V. Lebedev, T. S. Novikova, and S. S. Novikov, Khim. Geterotsikl. Soedin., 835 (1965).

  9. S. S. Novikov, L. I. Khmel'nitskii, T. S. Novikova, and O. V. Lebedev, Khim. Geterotsikl. Soedin., 590 (1970).

  10. O. Ya. Neiland and G. Ya. Vanag, Zh. Obshch. Khim.,31, 146 (1961).

    Google Scholar 

  11. R. C. Elderfield (editor), Heterocyclic Compounds, Vol. 1, Wiley, New York (1950), Chap. 8.

    Google Scholar 

  12. A. I. Ivanov, I. E. Chlenov, V. A. Tartakovskii, V. I. Slovetskii, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1491 (1965).

  13. A. W. Johnson, Ylide Chemistry, Academic Press, New York (1966).

    Google Scholar 

  14. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 139 (1977).

  15. C. Henrick, E. Ritchie, and W. Taylor, Austr. J. Chem.,20, 2455 (1967).

    Google Scholar 

  16. G. Koser and Shwn-Meei Yu, J. Org. Chem.,41, 125 (1976).

    Google Scholar 

  17. K. Nakanishi, Infrared Absorption Spectroscopy, Holden-Day, San Francisco (1962).

    Google Scholar 

  18. W. Middleton, J. Org. Chem.,31, 3731 (1966).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. V. Semenov & S. A. Shevelev

Authors
  1. V. V. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Shevelev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2355–2360, October, 1978.

For the preliminary data, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Semenov, V.V., Shevelev, S.A. Nitroylides 6. Transfer of a nitromethylene fragment with the aid of iodonium nitroylides. Russ Chem Bull 27, 2087–2092 (1978). https://doi.org/10.1007/BF00946533

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00946533

Keywords

Search

Navigation