Skip to main content
SpringerLink
Log in

1-Acyloxyaziridine-2,2-dicarboxylic acid esters

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of diazomethane and O-acylisonitrosomalonates gave Δ2-1,2,3-triazoline-5,5-dicarboxylic acid esters, the rates of formation and thermal stabilities of which are determined by the character of ths substituent attached to the oxygen atom. Thermolysis of the triazolines leads to mixtures of 1-acyloxyaziridine-2,2-dicarboxylic acid esters and isomeric dialkyl O-acylisonitrososuccinates; acidolysis with BF3·Et2O makes it possible to obtain exclusively aziridines. The acidic decompositions of dimethyl 4-methyl-Δ2-1,2,3-triazoline-5,5-dicarboxylate, which was obtained from the reaction of diazoethane and dimethyl O-tosylisonitrosomalonate, leads to dimethyl α-tosyloxyamino-α-vinylmalonate. A dependence of the spin-spin coupling constants (SSCC) of the protons of the aziridine ring on the electronegativities of the substituents attached to the oxygen atom was observed.

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. R. G. Kostyanovskii, V. F. Rudchenko, A. V. Prosyanik, M. D. Isohaev, I. I. Chervin, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 628 (1977).

    Google Scholar 

  2. R. G. Kostyanovskii and V. F. Rudchenko, Dokl. Akad. Nauk SSSR, 231, 878 (1976).

    Google Scholar 

  3. G. V. Shustov, N. B. Tavakalyan, N. L. Zaichenko, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2183 (1980).

    Google Scholar 

  4. R. G. Kostyanovskii, A. V. Prosyanik, A. I. Mishchenko, G. V. Shustov, I. I. Chervin, N. L. Zaichenko, A. P. Pleshkova, P. N. Belov, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1780 (1979).

    Google Scholar 

  5. J.-M. Biehler, J. Perchais, and J. -P. Fleury, Bull. Soc. Chim. Fr., No. 19, 2711 (1971).

    Google Scholar 

  6. A. Gordon and R. Ford, The Chemist's Companion, Wiley (1973).

  7. A. A. Kazitsina and N. B. Kuplet-skaya, Application of UV, IR, and NMR Spectroscopy in Organic Chemistry [in Russian], Vysshaya Shkola, Moscow (1971), p. 35.

    Google Scholar 

  8. J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High-Resolution NMR Spectroscopy, Pergamon, Oxford (1965).

    Google Scholar 

  9. R. G. Kostyanovskii, G. I. Kadorkina, G. V. Shustov, and K. S. Zakharov, Dokl. Akad. Nauk SSSR, 221, 370 (1975).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. F. É. Dzerzhinskii Dnepropetrovsk Institute of Chemical Technology, 320640, Dnepropetrovsk

    A. I. Mishchenko, A. V. Prosyanik, P. N. Belov, V. A. Romanchenko, E. G. Belova & V. I. Markov

Authors
  1. A. I. Mishchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Prosyanik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. N. Belov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Romanchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. G. Belova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. I. Markov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 338–342, March, 1984.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mishchenko, A.I., Prosyanik, A.V., Belov, P.N. et al. 1-Acyloxyaziridine-2,2-dicarboxylic acid esters. Chem Heterocycl Compd 20, 270–274 (1984). https://doi.org/10.1007/BF00515636

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00515636

Keywords

Search

Navigation