Skip to main content
Log in

Addition of chlorobromomalonic ester to methyl acrylate

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

Conclusions

  1. 1.

    The addition of chlorobromomalonic ester to methyl acrylate, initiated by the Fe(CO)5 + DMF system, proceeds with the cleavage of the C-Br bond in the addendum and the formation of (C2H5OOC)5CClCH2CHBr-COOCH3.

  2. 2.

    The chlorobromo- and dichloromalonic esters when treated with Fe(CO)5 are capable of cleaving both halogen atoms and, in the absence of an unsaturated compound, form tetraethyl ethylene tetracarboxylate, while with methyl acrylate they form l, l-dicarbethoxy-2-carbomethoxycyclopropane.

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.

Literature cited

  1. M. Conrad and C. Brückner, Ber.,24, 2993 (1891).

    Google Scholar 

  2. T. A. Pudova, F. K. Velichko, L. I. Terekhova, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 1354.

  3. F. K. Velichko, R. A. Amriev, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 1455.

  4. C. E. Coffey, J. Am. Chem. Soc.,83, 1623 (1961).

    Google Scholar 

  5. J. Furukawa, A. Matsumura, Y. Matsuoka, and J. Kiji, Bull. Chem. Soc. Jpn.,49, 829 (1976).

    Google Scholar 

  6. E. Ciganek, J. Org. Chem.,30, 4366 (1965).

    Google Scholar 

  7. R. Pelliciari and P. Cogolli, Synthesis,1975, 269.

  8. A. Bury and M. D. Johnson, J. Chem. Soc. Chem. Commun.,1980, 498.

  9. T. T. Vasil'eva, F. K. Velichko, G. A. Trapeznikova, Z. A. Abdulkina, R. A. Amriev, B. V. Nelyubin, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1981, 1075.

  10. Y. Kusuyama and Y. Ikeda, Bull. Chem. Soc. Jpn.,50, 1784 (1977).

    Google Scholar 

  11. Organic Syntheses, Coll. Vol. 2 [Russian translation], IL, Moscow (1949), p. 601.

  12. P. Krapcho and P. S. Huyffer, J. Org. Chem.,28, 2904 (1963).

    Google Scholar 

  13. S. Botros and M. Khalifa, Egypt J. Pharmac. Sci.,16, 57 (1975); Ref. Zh., Khim.,1977, 14 Zh, 44.

    Google Scholar 

  14. M. Conrad and M. Guthzeit, Ann. Chem.,214, 76 (1882).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2815–2818, December, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abdulkina, Z.A., Amriev, R.A. & Velichko, F.K. Addition of chlorobromomalonic ester to methyl acrylate. Russ Chem Bull 30, 2347–2349 (1981). https://doi.org/10.1007/BF00963709

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00963709

Keywords

Navigation