Skip to main content
SpringerLink
Log in

Homolytic addition of malonic and succinic acid esters to alkyl maleates

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

Conclusions

  1. 1.

    The methyl and ethyl esters of maleic acid form 1∶1 and 2∶1 adducts with the methyl and ethyl esters of malonic and succinic acids in a reaction initiated by tert-butyl peroxide with high conversion (from 85 to 100%) and yield (from 75 to 100%).

  2. 2.

    Ethyl malonate and the alkyl succinates form two types of adducts with the alkyl maleates as a result of addition at the α-carbon atoms of the acid and alcohol segments of the ester. The addition of methyl malonate to alkyl maleates occurs only at the methylene group.

  3. 3.

    The alkyl malonates and methyl succinate predominantly add two molecules of alkyl maleate.

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. H. H. Vogel, Synthesis, 90 (1970).

  2. A. D. Petrov, G. I. Nikishin, and Yu. N. Ogibin, Dokl. Akad. Nauk SSSR,131, 580 (1960); G. I. Nikishin, Yu. N. Ogibin, and A. D. Petrov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1326 (1961); Tr. Khim. Khim. Tekhnol.,4, 123 (1961); G. Maerker, J. Am. Oil Chem. Soc,43, 104 (1966).

    Google Scholar 

  3. J. C. Allan, J. I. G. Gadogan, B. W. Harris, and D. H. Hey, J. Cham. Soc., 4468 (1962); F. Asinger, B. Fell, and H. H. Vogel, Tetrahedron Lett., 3867 (1967).

  4. R. L. Huang, C. O. Ong, and S. H. Ong, J. Chem. Soc, C, 2217 (1968).

    Google Scholar 

  5. M. S. Kharasch, E. V. Jensen, and W. H. Urry, J. Org. Chem.,10, 386 (1945).

    Google Scholar 

  6. G. Anes, Organomet. Chem. Synth.,1, 93 (1970–71); Chem. Abstr.74, 75980 (1971).

    Google Scholar 

  7. R. Kh. Freidlina and A. B. Terent'ev, Accounts Chem. Res.,10, 9 (1977).

    Google Scholar 

  8. F. Minisci, R. Galli, M. Cecere, V. Malatesta, and T. Caronna, Tetrahedron Lett., 5609 (1966).

  9. N. M. Mikhailov, L. M. Rappoport, and S. Z. Taits, Inventor's Certificate No. 486,261 (1975); Byull. Izobr., No. 36, 108 (1975).

  10. L. M. Rappoport and S. Z. Taits, Izv. Akad. Nauk SSSR, Ser. Khim., 2175 (1975).

  11. N. A. Miles and D. M. Surgenor, J. Am. Chem. Soc.,68, 2079 (1961).

    Google Scholar 

  12. K. Alder and M. Schumacher, Liebigs Ann. Chem.,564, 96 (1949).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Yu. N. Ogibin, M. N. Élinson, G. I. Nikishin, V. I. Kadentsev & O. S. Chizhov

Authors
  1. Yu. N. Ogibin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. N. Élinson
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. I. Nikishin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Kadentsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. S. Chizhov
    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. 3, pp. 557–563, March, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ogibin, Y.N., Élinson, M.N., Nikishin, G.I. et al. Homolytic addition of malonic and succinic acid esters to alkyl maleates. Russ Chem Bull 28, 512–518 (1979). https://doi.org/10.1007/BF00924823

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00924823

Keywords

Search

Navigation