Skip to main content
Log in

On the mechanism of certain reactions proceeding with the participation of diazonium salts

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

Conclusions

  1. 1.

    The influence of substituents in the aryldiazonium cation on the yields of products of radical reactions and reactions proceeding according to a heterolytic mechanism was considered.

  2. 2.

    It was hypothesized that the Sandmeyer reaction proceeds according to a radical mechanism.

  3. 3.

    The heterolytic mechanism of the Nesmeyanov reaction was confirmed.

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. G. Zollinger, Chemistry of Azo-Dyes [Russian translation], GKhI, Moscow; 1960; B. A. Porai-Koshits, Uspekhi Khimii,28, 237 (1959).

    Google Scholar 

  2. E. S. Lewis and H. Suhr, Ber.92, 3031, 3043 (1959); C. D. Ritchie, J. D. Salteil, and E. S. Lewis, J. Amer. Chem. Soc.83, 4661 (1961).

    Google Scholar 

  3. J. F. Bunnet and R. E. Zahler, Chem. Rev.49, 297 (1951).

    Google Scholar 

  4. S. H. Euler, Liebigs Ann. Chem.325, 292 (1902).

    Google Scholar 

  5. M. L. Crossly, R. H. Kienle, and C. H. Benbrook, J. Amer. Chem. Soc.62, 1400, (1949).

    Google Scholar 

  6. E. S. Lewis and M. D. Johnson, J. Amer. Chem. Soc.81, 2076 (1959); E. S. Lewis and E. B. Miller J. Amer. Chem. Soc.75, 429 (1953).

    Google Scholar 

  7. W. E. Lee, J. G. Colvert, and E. V. Marmberg, J. Amer. Chem. Soc.,83, 1928, (1961).

    Google Scholar 

  8. D. F. De-Tar and M. N. Turetzki, J. Amer. Chem. Soc.77, 1745 (1955);78, 3928 (1956); D. F. DeTar, T. Kosuge, J. Amer. Chem. Soc.,80, 6073 (1958).

    Google Scholar 

  9. D. F. De-Tar, J. Amer. Chem. Soc.73, 1446 (1951).

    Google Scholar 

  10. L. Horner and H. Stohr, Ber.85, 993 (1952).

    Google Scholar 

  11. D. H. Hey, A. Nechvatai, and T. S. Robinson, J. Chem. Soc.1951, 2852; D. K. Augood, D. H. Hey, and G. H. Williems, J. Chem. Soc.1953, 44.

  12. J. Elks, J. W. Howorth, and G. H. Williems, J. Chem. Soc.1940, 1285.

  13. A. V. Dombrovskii, Uspekhi Khimii,26, 689 (1957).

    Google Scholar 

  14. O. Vogl and C. S. Rondestvedt, J. Amer. Chem. Soc.77, 3067 (1955); J. K. Kochi, J. Amer. Chem. Soc.79, 2949 (1957); G. N. Schrauser, Ber.94, 1891 (1961); S. C. Dickerman, K. Weiss, and A. K. Ingbermann, J. Organ. Chem.21, 380 (1956).

    Google Scholar 

  15. A. Roe, Organic Reactions [Russian translation], IL, Moscow, 1951, p. 155.

    Google Scholar 

  16. E. Pfeil, Angew. Chem.65, 155 (1953).

    Google Scholar 

  17. W. A. Cowdrey and D. S. Davies. J. Chem. Soc.1949, 549.

  18. E. Pfeil and O. Veiten, Liebigs Ann. Chem.565, 183 (1949).

    Google Scholar 

  19. W. A. Waters, Chemistry of Free Radicals [Russian translation], IL, Moscow, 1948, p. 178.

    Google Scholar 

  20. L. G. Makarova, Reactions and Methods of Investigating Organic Compounds [in Russian], GKhI, Moscow, 1954,3, p. 73.

    Google Scholar 

  21. O. A. Reutov, A. G. Markovskaya, and R. E. Mardaleishvili, Zh. Fiz. Khimii,30, 2533 (1956); O. A. Reutov, Izv. AN SSSR. Otd. Khim. N.,1956, 943.

    Google Scholar 

  22. A. N. Nesmeyanov, Zh. Russk. Fiz.-Khim. Obshch.,61, 1393 (1929).

    Google Scholar 

  23. A. N. Nesmeyanov and E. I. Kan, Zh. Russk. Fiz.-Khim. Obshch,61, 1407 (1929).

    Google Scholar 

  24. T. K. Ko'minskaya, M. M. Nad', and K. A. Kocheshkov, Zh. Obshch. Khimii,16, 891 (1946).

    Google Scholar 

  25. A. N. Nesmeyanov and L. G. Makarova, Dokl. AN SSSR,87, 421 (1952).

    Google Scholar 

  26. O. A. Reutov, Dokl. AN SSSR,87, 991 (1952); O. A. Reutov and Yu. G. Bundel', Zh. Obshch. Khimii,25, 2324 (1955).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 966–973, June, 1966.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kikot', V.S., Kazitsyna, L.A. & Reutov, O.A. On the mechanism of certain reactions proceeding with the participation of diazonium salts. Russ Chem Bull 15, 924–930 (1966). https://doi.org/10.1007/BF00846041

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00846041

Keywords

Navigation