Skip to main content
SpringerLink
Log in

Selectivity of the generation of 3- and 4-carboxyalkyl radicals from substituted glutaric and adipic acids and their oxidative lactonization

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

Conclusions

  1. 1.

    The oxidative decarboxylation of acids with carboxyl groups at secondary and tertiary C atoms under the action of the S2O8 2−- Ag+ and S2O8 2−-Ag+- Cu2+ systems is at least an order of magnitude faster than that of acids with COOH groups at a primary C atom, as a result of which 3- and 4-carboxyalkyl radicals with the general formula R'RĊ(CH2)nCOOH (R is alkyl or phenyl, R′ is H or alkyl, n=2 or 3) are generated with > 90% selectivity from 2-substituted glutaric and adipic acids.

  2. 2.

    The 3- and 4-carboxyalkyl radicals are completely or partially converted under their generation conditions into lactones. The selectivity of the oxidative lactonization increases from 0.30 to 0.97 along the series of radicals C2H5ĊH(CH2)3COOH, C2H5ĊH(CH2)2COOH, ĊH2(CH2)3COOH, ĊH2(CH2)2COOH, (CH3)2Ċ(CH2)2-COOH, and C2H5ĊH(CH2)2COOH in the case of the S2O8 2−-Ag+ system and from 0.72 to 1 along this series in the case of the S2O8 2−- Ag+- Cu2+ system.

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. J. M. Anderson and J. K. Kochi, J. Am. Chem. Soc.,92, 1651 (1970).

    Google Scholar 

  2. C. Walling and D. M. Camaioni, J. Org. Chem.,43, 3266 (1978).

    Google Scholar 

  3. Yu. N. Ogibin, É. I. Troyanskii, and G. N. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 2239.

  4. Yu. N. Ogibin, É. I. Troyanskii, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 2522.

  5. Yu. N. Ogibin, É. I. Troyanskii, G. I. Nikishin, V. I. Kadentsev, and O. S. Chizhov, Izv. Akad. Nauk SSSR, Khim.,1975, 967.

  6. Yu. N. Ogibin, É. I. Troyanskii, E. K. Starostin, S. I. Moryashova, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 933.

  7. Yu. N. Ogibin, M. I. Katsin, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 1975, 1345.

  8. G. S. King and E. S. Waight, J. Chem. Soc. Perkin Trans,1, 1974, 1499.

    Google Scholar 

  9. E. Honkanen, J. Moisio, and P. Karvonen, Acta Chem. Scand.,19, 370 (1965).

    Google Scholar 

  10. R. N. Jones, C. L. Angell, T. Ito, and R. J. Smith, Can. J. Chem.,37, 2007 (1959).

    Google Scholar 

  11. J. C. Bardham, J. Chem. Soc.,1940, 848.

  12. G. I. Nikishin, R. A. Somov, and A. D. Petrov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk,1961, 2065.

  13. N. H. Cromwell, P. L. Creger, and K. E. Cook, J. Am. Chem. Soc.,78, 4412 (1956).

    Google Scholar 

  14. J. R. Johnson and O. H. Johnson, J. Am. Chem. Soc.,62, 2615 (1940).

    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, É. I. Troyanskii, V. I. Kadentsev, E. D. Lubuzh, O. S. Chizhov & G. I. Nikishin

Authors
  1. Yu. N. Ogibin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. É. I. Troyanskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Kadentsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. D. Lubuzh
    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

  6. G. I. Nikishin
    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. 5, pp. 1070–1075, May, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ogibin, Y.N., Troyanskii, É.I., Kadentsev, V.I. et al. Selectivity of the generation of 3- and 4-carboxyalkyl radicals from substituted glutaric and adipic acids and their oxidative lactonization. Russ Chem Bull 30, 830–834 (1981). https://doi.org/10.1007/BF00955294

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00955294

Keywords

Search

Navigation