Skip to main content
Log in

Pyramidal amide nitrogen in N-acyldiaziridines and N-acyloxaziranes

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

Conclusions

The pyrimidal stability of the amide nitrogen increases in the order: N-acylaziridines, N-acyldiaziridines, and N-acyloxaziranes.

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.

Similar content being viewed by others

Literature cited

  1. H. Pracejus, Chem. Ber.,92, 988 (1959); Tetrahedron,21, 2257 (1965); R. G. Kostyanovsky, E. E. Mikhlina, and L. N. Yakhontov, Organic Mass Spectrometry,3, 1023 (1970).

    Google Scholar 

  2. T. H. Siddall and C. A. Prohaska, Nature,208, 582 (1965); T. H. Siddall and W. E. Stewart, Progress in Nuclear Magnetic Resonance Spectroscopy, J. W. Emsley, J. Feeney, and L. H. Sutcliffe (editors), Pergamon Press, Oxford (1970), Chap. 2, p. 64.

    Google Scholar 

  3. E. I. Levkoeva and L. N. Yakhontov, Usp. Khim.,41, 1337 (1972).

    Google Scholar 

  4. R. P. Shibaeva, L. O. Atovmyan, and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,175, 586 (1967); Sixth International Congress and Symposium on Crystal Growth, Abstracts of Papers [in Russian], Nauka (1966), p. 21; L. V. Vilkov, I. I. Nazarenko, and R. G. Kostyanovskii, Zh. Struk. Khim.,9, 1075 (1968).

    Google Scholar 

  5. R. G. Kostyanovskii and V. F. Bystrov, Dokl. Akad. Nauk SSSR,148, 839 (1963); Opt. I Spektr.,19, 217 (1965); F. A. L. Anet and J. M. Osyany, J. Amer. Chem. Soc.,89, 353 (1967).

    Google Scholar 

  6. T. Z. Papoyan, I. I. Chervin, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1530 (1968); O. A. Yuzhakova, V. F. Bystrov, and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,147, 843 (1962); Izv. Akad. Nauk SSSR, Ser. Khim., 242 (1966); R. G. Kostyanovsky, K. S. Zakharov, M. Zaripova, and V. F. Rudtchenko, Tetrahedron Lett., 4207 (1974).

  7. A. Mannschreck and W. Seitz, Angew. Chem.,81, 224 (1969); R. G. Kostyanovskii, A. E. Potyakov, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., 1671 (1974); 198 (1975); Dokl. Akad. Nauk SSSR, 219, 873 (1974); J. Bjørgo and D. R. Boyd, J. Chem. Soc., Perkin Trans., II, 1575 (1973).

    Google Scholar 

  8. M. Jautelat and J. D. Roberts, J. Amer. Chem. Soc.,91, 642 (1969).

    Google Scholar 

  9. A. Mannschreck, R. Radeglia, E. Gründemann, and R. Ohme, Chem. Ber.,100, 1778 (1967).

    Google Scholar 

  10. R. G. Kostyanovskii, O. A. Yuzhakova, and V. F. Bystrov, Zh. Vses. Khim, Obshchestva im. D. I. Mendeleeva,10, 229 (1965); R. G. Kostyanovskii, O. A. Pan'shin, and T. Z. Papoyan, Dokl. Akad. Nauk SSSR,177, 1099 (1967); R. G. Kostyanovsky, Z. E. Samojlova, and I. I. Tchervin, Tetrahedron Lett., 3025 (1968).

    Google Scholar 

  11. R. G. Kostyanovskii, Z. E. Samoilova, M. Zaripova, and A. P. Pleshkova, Dokl. Akad. Nauk SSSR,218, 1100 (1974).

    Google Scholar 

  12. E. Schmitz and R. Ohme, Chem. Ber.,94, 2166 (1961); E. Schmitz, Three-Membered Rings with Two Heteroatoms [Russian translation], Mir (1970), p. 136.

    Google Scholar 

  13. J. V. Karabinos and K. T. Serijan, J. Amer. Chem. Soc.,67, 1856 (1945); T. L. Cairns, J. Amer. Chem. Soc.,63, 871 (1941).

    Google Scholar 

  14. E. Schmitz, R. Ohme, and S. Schramm, Chem. Ber.,97, 2521 (1964).

    Google Scholar 

  15. D. R. Boyd, R. Spratt, and D. M. Jerina, J. Chem. Soc., C 2650 (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 875–884, April, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kostyanovskii, R.G., Zakharov, K.S., Zaripova, M. et al. Pyramidal amide nitrogen in N-acyldiaziridines and N-acyloxaziranes. Russ Chem Bull 24, 791–799 (1975). https://doi.org/10.1007/BF00920695

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00920695

Keywords

Navigation