Skip to main content
Log in

Structure of products of the reaction of 2-cyanoaziridine with carbonyl compounds

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The structure of azimexone (3), the product of the reaction of 2-cyanoaziridine with acetone, was confirmed on the basis of1H and13C NMR spectra. The formation of this product is accounted for by the α-aziridinoalkylating action of an intermediate containing a good leaving iminoyloxy group. Similar reactions were observed for 1-chloromethylaziridine and a 1-aziridinylmethylammonium salt (6), but not for 1-methoxymethylaziridine (7) and 1-aziridinemethanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. K. D. Friedberg, K. Mengel, and E. Schlick,Radiat. Environ. Biophys., 1983,22, 117.

    Google Scholar 

  2. E. Schlick, R. Ruffmann, K. Hartung, and M. A. Chirigos,Int. J. Immunopharm., 1985,7, 141.

    Google Scholar 

  3. U. Bicker, K. D. Friedberg, G. Hebold, and K. Mendel,Experimentia, 1979,35, 1361.

    Google Scholar 

  4. M. A. Chirigos and M. L. Patchen,Pharm. Ther., 1988,39, 243.

    Google Scholar 

  5. W. Kampe, M. Thiel, E. Fauland, U. Bicker, and G. Hebold, USSR Pat. 673167,Byull. Izobret., 1979, No. 25, 234 (in Russian).

    Google Scholar 

  6. R. Bartnik, S. Lesniak, and J. Krzywanski,Pol. J. Chem., 1978,52, 407.

    Google Scholar 

  7. K. Jähnisch, E. Schmitz, and E. Gründemann,J. Prakt. Chem., 1979,321, 712.

    Google Scholar 

  8. A. A. Fomichev and R. G. Kostyanovsky,Dokl. Akad. Nauk SSSR, 1971,199, 1110 [Dokl. Chem., 1971,199 (Engl. Transl.)].

    Google Scholar 

  9. R. G. Kostyanovsky, A. P. Pleshkova, V. N. Voznesensky, A. V. Prosyanik, G. K. Kadorkina, and V. F. Rudchenko,Khim. Geterotsikl. Soedin., 1977, 624 [Chem. Heterocycl. Comp., 1977 (Engl. Transl.)].

  10. I. I. Chervin, A. A. Fomichev, A. S. Moskalenko, N. L. Zaichenko, A. E. Aliev, A. V. Prosyanik, V. N. Voznesensky, and R. G. Kostyanovsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 1110 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988,37, 972 (Engl. Transl.)].

    Google Scholar 

  11. B. Sunners, L. H. Piette, and W. G. Schneider,Can. J. Chem., 1960,38, 681.

    Google Scholar 

  12. A. V. Ioganson, inVodorodnaya svyaz' [Hydrogen Bond], Nauka, Moscow, 1989 (in Russian).

    Google Scholar 

  13. S. V. Varlamov, G. K. Kadorkina, and R. G. Kostyanovsky,Khim. Geterotsikl. Soedin., 1988, 390 [Chem. Heterocycl. Comp., 1988 (Engl. Transl.)].

  14. R. G. Kostyanovsky and O. A. Pan'shin,Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 740 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1965, 721 (Engl. Transl.)].

  15. K. Jähnisch, F. Gründemann, and A. Kunath,XIII Intern. Sympos. muleSynthesis in Organic Chemistrymule, Oxford, June 20–22, 1993.

  16. R. G. Kostyanovsky and O. A. Pan'shin,Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 567 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1965, 553 (Engl. Transl.)].

  17. R. G. Kostyanovsky, D. Sc. Thesis, N. N. Semenov Institute of Chemical Physics, RAS, Moscow, 1968.

    Google Scholar 

  18. V. F. Rudchenko, S. M. Ignatov, and R. G. Kostyanovsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1153 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 1045 (Engl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2136–2139, December, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koehler, K.F., Zaddach, H., Kadorkina, G.K. et al. Structure of products of the reaction of 2-cyanoaziridine with carbonyl compounds. Russ Chem Bull 42, 2049–2052 (1993). https://doi.org/10.1007/BF00698898

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00698898

Key words

Navigation