Skip to main content

Aromatic Substitution

  • Chapter

Abstract

Electrophilic aromatic substitution reactions are important for synthetic purposes, and they also represent one of the most thoroughly studied classes of organic reactions from a mechanistic point of view. The synthetic aspects of these reactions are discussed in Part B. The discussion here will emphasize the mechanisms of several of the most completely studied reactions. These mechanistic ideas lay the groundwork for the extensive study that has been done on structure-reactivity relationships in aromatic electrophilic substitution. This topic will be discussed in Section 10.2.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

  • R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York, 1967.

    Google Scholar 

  • J. G. Hoggett, R. B. Moodie,J.R. Penton, and K. S. Schofield, Nitration and Aromatic Reactivity, Cambridge University Press, Cambridge, 1971.

    Google Scholar 

  • C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, New York, 1969, Chapter VI.

    Google Scholar 

  • J. Miller, Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968.

    Google Scholar 

  • R. O. C. Norman and R. Taylor, Electrophilic Substitution in Benzenoid Compounds, Elsevier, Amsterdam, 1965.

    Google Scholar 

  • G. A. Olah, Friedel-Crafts Chemistry, Wiley, New York, 1973.

    Google Scholar 

  • S. Patai (ed.), The Chemistry of Diazonium and Diazo Groups, Wiley, New York, 1978.

    Google Scholar 

  • R. M. Roberts and A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York, 1984.

    Google Scholar 

  • L. M. Stock, Aromatic Substitution Reactions, Prentice-Hall, Englewoods Cliffs, New Jersey, 1968.

    Google Scholar 

References for Problems

  1. C. K. Ingold and E. H. Ingold,J. Chem. Soc., 2249 (1928).

    Google Scholar 

  2. R. J. Albers and E. C. Kooyman, Rec. Trav. Chim. 83, 930 (1964).

    Article  CAS  Google Scholar 

  3. J. R. Knowles and R. O. C. Norman,J. Chem. Soc., 2938 (1961).

    Google Scholar 

  4. A. Gastaminza, T. A. Modro, J. H. Ridd, and J. H. P. Utley,J. Chem. Soc, B, 534 (1968).

    Google Scholar 

  5. J. R. Knowles, R. O. C. Norman, and G. K. Radda,J. Chem. Soc, 4885 (1960).

    Google Scholar 

  6. F. L. Riley and E. Rothstein,J. Chem. Soc, 4885 (1960).

    Google Scholar 

  7. T. C. van Hoek, P. E. Verkade, and B. M. Wepster, Rev. Trav. Chim. 77, 559 (1958);

    Article  Google Scholar 

  8. A. van Loon, P. E. Verkade, and B. M. Wepster, Rec. Trav. Chim. 79, 977 (1960).

    Article  Google Scholar 

  9. G. A. Olah, S. J. Kuhn, S. H. Flood, and J. C. Evans,J. Am. Chem. Soc. 84, 3687 (1962).

    Article  CAS  Google Scholar 

  10. J. E. Dubois, J. J. Aaron, P. Alcais, J. P. Doucet, F. Rothenberg, and R. Uzan,J. Am. Chem. Soc. 94, 6823 (1972).

    Article  CAS  Google Scholar 

  11. R. M. Roberts and D. Shiengthong,J. Am. Chem. Soc. 86, 2851 (1964).

    Article  CAS  Google Scholar 

  12. R. L. Dannley, J. E. Gagen, and K. Zak,J. Org. Chem. 38, 1 (1973);

    Article  CAS  Google Scholar 

  13. R. L. Dannley and W. R. Knipple,J. Org. Chem. 38, 6 (1973).

    Article  CAS  Google Scholar 

  14. C. D. Gutsche and K. H. No,J. Org. Chem. 47, 2708 (1982).

    Article  CAS  Google Scholar 

  15. G. D. Figuly and J. C. Martin,J. Org. Chem. 45, 3728 (1980).

    Article  CAS  Google Scholar 

  16. K. Key, C. Eaborn, and D. R. M. Walton, Organomet. Chem. Synth. 1, 151 (1970–1971).

    Google Scholar 

  17. S. Winstein and R. Baird,J. Am. Chem. Soc. 79, 756 (1957).

    Article  CAS  Google Scholar 

  18. D. S. Noyce, P. A. Kittle, and E. H. Bannitt,J. Org. Chem. 33, 1500 (1958).

    Article  Google Scholar 

  19. M. Essiz, G. Guillaumet, J.-J. Brunet, and P. Caubere,J. Org. Chem. 45, 240 (1980).

    Article  CAS  Google Scholar 

  20. W. Nagata, K. Okada, and T. Akoi, Synthesis, 365 (1979).

    Google Scholar 

  21. W. G. Miller and C. U. Pittman Jr.,J. Org. Chem. 39, 1955 (1974).

    Article  CAS  Google Scholar 

  22. T. A. Modro and K. Yates,J. Am. Chem. Soc. 98, 4247 (1976).

    Article  CAS  Google Scholar 

  23. A. V. R. Rao, V. H. Deshpande, and N. L. Reddy, Tetrahedron Lett., 4373 (1982).

    Google Scholar 

  24. L. M. Jackman and V. R. Haddon,J. Am. Chem. Soc. 96, 5130 (1974);

    Article  CAS  Google Scholar 

  25. M. Gates, D. L. Frank, and W. C. von Feiten,J. Am. Chem. Soc. 96, 5138 (1974).

    Article  CAS  Google Scholar 

  26. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Second Edition, Cornell University Press, Ithaca, New York, 1969, pp. 340–344;

    Google Scholar 

  27. C. G. Swain and D. R. Crist,J. Am. Chem. Soc 94, 3195 (1972).

    Article  CAS  Google Scholar 

  28. M. L. Bird and C. K. Ingold,J. Chem. Soc, 918 (1938);

    Google Scholar 

  29. J. D. Roberts, J. K. Sanford, F. L. J. Sixma, H. Cerfontain, and R. Zagt,J. Am. Chem. Soc. 76, 4525 (1954).

    Article  CAS  Google Scholar 

  30. E. Baciocchi, F. Cacace, G. Ciranni, and G. Illuminati,J. Am. Chem. Soc. 94, 7030 (1972).

    Article  CAS  Google Scholar 

  31. R. B. Moodie and K. Schofield, Acc. Chem. Res. 9, 287 (1976).

    Article  CAS  Google Scholar 

  32. P. C. Myhre, M. Beug, and L. L. James,J. Am. Chem. Soc. 90, 2105 (1968).

    Article  CAS  Google Scholar 

  33. L. R. C. Barclay, B. A. Ginn, and C. E. Milligan, Can. J. Chem. 42, 579 (1964).

    Article  CAS  Google Scholar 

  34. A. A. Khalaf and R. M. Roberts,J. Org. Chem. 34, 3571 (1969);

    Article  CAS  Google Scholar 

  35. A. A. Khalaf, Rev. Chim. (Bucharest) 19, 1373 (1974).

    CAS  Google Scholar 

  36. G. P. Stahly,J. Org. Chem. 50, 3091 (1985).

    Article  CAS  Google Scholar 

  37. A. I. Meyers and P. D. Pansegrau, Tetrahedron Lett. 24, 4935 (1983).

    Article  CAS  Google Scholar 

  38. M. Maksoza and J. Winiarski,J. Org. Chem. 49, 1494 (1984).

    Article  Google Scholar 

  39. I. J. Anthony and D. Wege, Aust. J. Chem. 37, 1283 (1984).

    Article  CAS  Google Scholar 

  40. Y. Konayashi, T. Nagai, I. Kumadaki, M. Takahashi, and T. Yamauchi, Chem. Pharm. Bull. 32, 4382 (1984).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Plenum Press, New York

About this chapter

Cite this chapter

Carey, F.A., Sundberg, R.J. (1990). Aromatic Substitution. In: Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9795-3_10

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-9795-3_10

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-43447-1

  • Online ISBN: 978-1-4613-9795-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics