Skip to main content
Log in

Homolytic aromatic halogenation in the high energy region and the reactivity-selectivity principle

  • Published:
Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

The interaction between the halogen atom and the aromatic substrate, responsible for the deviation from the Reactivity-Selectivity Principle in homolytic aromatic halogenation in the high energy region (hot homolytic aromatic halogenation) is discussed.

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

References

  1. A. PROSS, Adv. Phys. Org. Chem., 14 (1977) 69.

    Google Scholar 

  2. C. WALLING, M. F. MAYAHI, J. Amer. Chem. Soc., 81 (1959) 1485.

    Article  Google Scholar 

  3. R. J. CVETANOVIC, J. Chem. Phys., 30 (1959) 19.

    Article  Google Scholar 

  4. F. MINISCI, A. CITTERIO, Adv. Free-Radical Chem., 6 (1980) 65.

    Google Scholar 

  5. G. A. OLAH, Intern. Symp. on Organic Reaction Mechnisms, Cork, Ireland, July 1964. Spec. Publ. No. 19, The Chemical Society, Burlington House, London 1965, p. 57.

    Google Scholar 

  6. D. S. KEMP, M. L. CASEY, J. Amer. Chem. Soc., 95 (1973) 6670.

    Article  Google Scholar 

  7. T. J. GILBERT, C. D. JOHNSON, J. Amer. Chem. Soc., 96 (1974) 5846.

    Article  Google Scholar 

  8. C. D. JOHNSON, Chem. Rev., 75 (1975) 755.

    Article  Google Scholar 

  9. G. H. WILLIAMS, Homolytic Aromatic Substitution, International Series of Monographs on Organic Chemistry, P. H. R. BARTON, W. DOERING (Eds), Pergamon Press, London 1960.

    Google Scholar 

  10. J. MARCH, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 2nd ed. Mc-Graw-Hill, London, p. 629.

  11. E. C. KOOYMAN, Pure Appl. Chem., 7 (1963) 193.

    Google Scholar 

  12. R. LOUW, G'INT. VELD, W. DORREPAAL, J. Chem. Soc. Perkin II, 2 (1973) 3610.

    Google Scholar 

  13. W. DORREPAAL, R. LOUW, Int. J. Chem. Kinet., 10 (1978) 249.

    Article  Google Scholar 

  14. C. L. PERRIN, G. A. SKINNER, J. Amer. Chem. Soc., 93 (1971) 3389.

    Article  Google Scholar 

  15. P. GOUVERNEUR, J. P. SOUMILLION, Tetrahedron Lett., No. 2 (1976) 133.

    Article  Google Scholar 

  16. J. G. TRAYNHAM, Tetrahedron Lett., No. 26 (1976) 2213 and (1977) 226 (correction).

    Article  Google Scholar 

  17. C. R. EVERLY, J. G. TRAYNHAM, J. Org. Chem., 44 (1979) 1784.

    Article  Google Scholar 

  18. J. G. TRAYNHAM, Chem. Rev., 79 (1979) 323.

    Article  Google Scholar 

  19. M. TIECCO, Acc. Chem. Res., 13 (1980) 51.

    Article  Google Scholar 

  20. R. D. GANDOUR, Tetrahedron, 36 (1980) 1001.

    Article  Google Scholar 

  21. M. TIECCO, Pure Appl. Chem., 53 (1981) 239.

    Google Scholar 

  22. J. G. TRAYNHAM, J. Chem. Educ., 60 (1983) 937.

    Google Scholar 

  23. E. A. GASPARAKIS, J. Chem. Educ., 63 (1986) 847.

    Google Scholar 

  24. C. M. WAI, F. S. ROWLAND, J. Amer. Chem. Soc., 90 (1968) 3638.

    Article  Google Scholar 

  25. G. STÖCKLIN, Hot Atom Chemistry Status Report, IAEA, Vienna 1974, p. 161.

  26. G. A. BRINKMAN, Chem. Rev., 81 (1981) 267.

    Article  Google Scholar 

  27. G. A. BRINKMAN, Int. J. Appl. Radiation Isotopes, 34 (1983) 985.

    Article  Google Scholar 

  28. K. BEREI, G. STÖCKLIN, Radiochim. Acta, 15 (1971) 39.

    Google Scholar 

  29. S. S. KONTIS, E. A. GASPARAKIS, Radiochim. Acta, 36 (1984) 103.

    Google Scholar 

  30. G. A. BRINKMAN, J. TH. VEENBOER, J. VISSER, F. M. KASPERSEN, L. LINDER, Radiochim. Acta, 26 (1979) 85.

    Google Scholar 

  31. S. J. RAND, R. L. STRONG, J. Amer. Chem. Soc., 82 (1960) 5.

    Article  Google Scholar 

  32. R. L. STRONG, S. J. RAND, J. A. BRITT, J. Amer. Chem. Soc., 82 (1960) 5053.

    Article  Google Scholar 

  33. R. E. Bupühler, M. EBERT, Nature, 214 (1967) 1221.

    PubMed  Google Scholar 

  34. G. A. OLAH, S. J. KUHN, S. H. FLOOD, J. Amer. Chem. Soc., 83 (1961) 4571.

    Article  Google Scholar 

  35. G. A. OLAH, S. J. KUHN, S. H. FLOOD, J. Amer. Chem. Soc., 83 (1961) 4581.

    Article  Google Scholar 

  36. H. H. COENEN, H. J. MACHULLA, G. STÖCKLIN, J. Amer. Chem. Soc., 99 (1977) 2892.

    Article  Google Scholar 

  37. G. A. RUSSELL, J. Amer. Chem. Soc., 79 (1957) 2977.

    Article  Google Scholar 

  38. G. A. RUSSELL, J. Amer. Chem. Soc., 80 (1958) 4987.

    Article  Google Scholar 

  39. G. A. RUSSELL, J. Amer. Chem. Soc., 80 (1958) 4997.

    Article  Google Scholar 

  40. G. A. RUSSELL, J. Amer. Chem. Soc., 80 (1958) 5002.

    Article  Google Scholar 

  41. G. A. RUSSELL, Tetrahedron, 8 (1960) 101.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to the memory of PATEROMANOLIS.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gasparakis, E.A. Homolytic aromatic halogenation in the high energy region and the reactivity-selectivity principle. Journal of Radioanalytical and Nuclear Chemistry, Articles 120, 267–274 (1988). https://doi.org/10.1007/BF02037341

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02037341

Keywords

Navigation