Skip to main content
SpringerLink
Log in

Aromatic Substitution Reactions

  • Chapter
Advanced Organic Chemistry

Part of the book series: Advanced Organic Chemistry ((AOCB))

Abstract

This chapter is concerned with reactions that introduce substituent groups on aromatic rings. The most important group of such reactions is the electrophilic aromatic substitutions, but there are also important reactions which occur by nucleophilic substitution. The mechanism of electrophilic aromatic substitution has been studied in great detail, and much information is available about structure-reactivity relationships. These areas were discussed in Chapter 10 of Part A. In this chapter, the synthetic aspects of aromatic substitution will be emphasized.

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

Access this chapter

Log in via an institution
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

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

Electrophilic Aromatic Substitution

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

    Google Scholar 

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

    Google Scholar 

  • G. A. Olah (ed.), Friedel-Crafts and Related Reactions, Vols. I–IV, Wiley-Interscience, New York, 1962–1964.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  • K. Schofield, Aromatic Nitration, Cambridge University Press, Cambridge, UK, 1980.

    Google Scholar 

  • L. M. Stock, Atomatic Substitution Reactions, Prentice-Hall, Englewood Cliffs, New Jersey, 1968.

    Google Scholar 

Nucleophilic Aromatic Substitution

  1. R. W. Hoffman, Dehydrobenzene and Cycloalkynes, Academic Press, New York, 1967.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  4. K. H. Saunders and R. L. M. Allen, Aromatic Diazo Compounds, Edward Arnold, London, 1985.

    Google Scholar 

  5. H. Zollinger, Azo and Diazo Chemistry, Interscience, New York, 1961.

    Google Scholar 

  6. L. Friedman and H. Shechter, J. Org. Chem. 26, 2522 (1961).

    Article  CAS  Google Scholar 

  7. E. C. Taylor, F. Kienzle, R. L. Robey, and A. McKillop, J. Am. Chem. Soc. 92, 2175 (1970).

    Article  CAS  Google Scholar 

  8. G. F. Hennion and S. F. de C. McLeese, J. Am. Chem. Soc. 64, 2421 (1942).

    Article  CAS  Google Scholar 

  9. J. Koo, J. Am. Chem. Soc. 75, 1889 (1953).

    Article  CAS  Google Scholar 

  10. E. C. Taylor, F. Kienzle, R. L. Robey, A. McKillop, and J. D. Hunt, J. Am. Chem. Soc. 93, 4845 (1971).

    Article  CAS  Google Scholar 

  11. G. A. Ropp and E. C. Coyner, Org. Synth. IV, 727 (1963).

    Google Scholar 

  12. M. Shiratsuchi, K. Kawamura, T. Akashi, M. Fujij, H. Ishihama, and Y. Uchida, Chem. Pharm. Bull. 35, 632 (1987).

    Article  CAS  Google Scholar 

  13. D. C. Furlano and K. D. Kirk, J. Org. Chem. 51, 4073 (1986).

    Article  CAS  Google Scholar 

  14. C. K. Bradsher, F. C. Brown, and H. K. Porter, J. Am. Chem. Soc. 76, 2357 (1954).

    Article  CAS  Google Scholar 

  15. E. C. Taylor, E. C. Bigham, and D. K. Johnson, J. Org. Chem. 42, 362 (1977).

    Article  CAS  Google Scholar 

  16. P. Studt, Justus Liebigs Ann. Chem., 2105 (1978).

    Google Scholar 

  17. T. Jojima, H. Takeshiba, and T. Kinoto, Bull. Chem. Soc. Jpn. 52, 2441 (1979).

    Article  CAS  Google Scholar 

  18. R. W. Bost and F. Nicholson, J. Am. Chem. Soc. 57, 2368 (1935).

    Article  CAS  Google Scholar 

  19. H. Dürr, H. Nickels, L. A. Pacala, and M. Jones, Jr., J. Org. Chem. 45, 973 (1980).

    Article  Google Scholar 

  20. C. L. Perrin and G. A. Skinner, J. Am. Chem. Soc. 93, 3389 (1971).

    Article  CAS  Google Scholar 

  21. R. A. Rossi and J. F. Bunnett, J. Am. Chem. Soc. 94, 683 (1972).

    Article  CAS  Google Scholar 

  22. M. Jones, Jr., and R. H. Levin, J. Am. Chem. Soc. 91, 6411 (1969).

    Article  CAS  Google Scholar 

  23. Y. Naruta, Y. Nishigaichi, and K. Maruyama, J. Org. Chem. 53, 1192 (1988).

    Article  CAS  Google Scholar 

  24. S. P. Khanapure, R. T. Reddy, and E. R. Biehl, J. Org. Chem. 52, 5685 (1987).

    Article  CAS  Google Scholar 

  25. G. Büchi and J. C. Leung, J. Org. Chem. 51, 4813 (1986).

    Article  Google Scholar 

  26. M. P. Doyle, J. F. Dellaria, Jr., B. Siegfried, and S. W. Bishop, J. Org. Chem. 42, 3494 (1977).

    Article  CAS  Google Scholar 

  27. T. Cohen, A. G. Dietz, Jr., and J. R. Miser, J. Org. Chem. 42, 2053 (1977).

    Article  CAS  Google Scholar 

  28. M. P. Doyle, B. Siegfried, R. C. Elliot, and J. F. Dellaria, Jr., J. Org. Chem. 42, 2431 (1977).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. E. McDonald and R. D. Wylie, Tetrahedron 35, 1415 (1979).

    Article  CAS  Google Scholar 

  31. M. P. Doyle, B. Siegfried, and J. F. Dellaria, Jr., J. Org. Chem. 42, 2426 (1977).

    Article  CAS  Google Scholar 

  32. A. P. Kozikowski, M. N. Greco, and J. P. Springer, J. Am. Chem. Soc. 104, 7622 (1982).

    Article  CAS  Google Scholar 

  33. P. H. Gore and I. M. Khan, J. Chem. Soc, Perkin Trans. 1, 2779 (1979).

    Google Scholar 

  34. A. A. Leon, G. Daub, and I. R. Silverman, J. Org. Chem. 49, 4544 (1984).

    Article  CAS  Google Scholar 

  35. S. R. Wilson and L. A. Jacob, J. Org. Chem. 51, 4833 (1986).

    Article  CAS  Google Scholar 

  36. S. A. Khan, M. A. Munawar, and M. Siddiq, J. Org. Chem. 53, 1799 (1988).

    Article  CAS  Google Scholar 

  37. J. R. Beadle, S. H. Korzeniowski, D. E. Rosenberg, B. J. Garcia-Slanga, and G. W. Gokel, J. Org. Chem. 49, 1594 (1984).

    Article  CAS  Google Scholar 

  38. B. L. Zenitz and W. H. Hartung, J. Org. Chem. 11, 444 (1946).

    Article  CAS  Google Scholar 

  39. T. F. Buckley III and H. Rapoport, J. Am. Chem. Soc. 102, 3056 (1980).

    Article  CAS  Google Scholar 

  40. G. A. Olah and J. A. Olah, J. Am. Chem. Soc. 98, 1839 (1976).

    Article  CAS  Google Scholar 

  41. E. J. Corey, S. Barcza, and G. Klotmann, J. Am. Chem. Soc. 91, 4782 (1969).

    Article  CAS  Google Scholar 

  42. E. C. Taylor, F. Kienzle, R. L. Robey, and A. McKillop, J. Am. Chem. Soc. 92, 2175 (1970).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  44. S. P. Khanapure, L. Crenshaw, R. T. Reddy, and E. R. Biehl, J. Org. Chem. 53, 4915 (1988).

    Article  CAS  Google Scholar 

  45. J. H. Boyer and R. S. Burkis, Org. Synth. V, 1067 (1973).

    Google Scholar 

  46. H. P. Schultz, Org. Synth. IV, 364 (1963); F. D. Gunstone and S. H. Tucker, Org. Synth. IV, 160 (1963).

    Google Scholar 

  47. D. H. Hey and M. J. Perkins, Org. Synth. V, 51 (1973).

    Google Scholar 

  48. K. Rorig, J. D. Johnston, R. W. Hamilton, and T. J. Telinski, Org. Synth. IV, 576 (1963).

    Google Scholar 

  49. K. G. Rutherford and W. Redmond, Org. Synth. V, 133 (1973).

    Google Scholar 

  50. M. M. Robinson and B. L. Robinson, Org. Synth. IV, 947 (1963).

    Google Scholar 

  51. R. Adams, W. Reifschneider, and A. Ferretti, Org. Synth. V, 107 (1973).

    Google Scholar 

  52. G. H. Cleland, Org. Synth. 51, 1 (1971).

    CAS  Google Scholar 

  53. R. E. Ireland, C. A. Lipinski, C. J. Kowalski, J. W. Tilley, and D. M. Walba, J. Am. Chem. Soc. 96, 3333 (1974).

    Article  CAS  Google Scholar 

  54. J. J. Korst, J. D. Johnston, K. Butler, E. J. Bianco, L. H. Conover, and R. B. Woodward, J. Am. Chem. Soc. 90, 439 (1968).

    Article  CAS  Google Scholar 

  55. K. A. Parker and J. Kallmerten, J. Org. Chem. 45, 2614, 2620 (1980).

    Article  CAS  Google Scholar 

  56. F. A. Carey and R. M. Guiliano, J. Org. Chem. 46, 1366 (1981).

    Article  CAS  Google Scholar 

  57. R. B. Woodward and T. R. Hoye, J. Am. Chem. Soc. 99, 8007 (1977).

    Article  CAS  Google Scholar 

  58. E. C. Horning, J. Koo, M. S. Fish, and G. N. Walker, Org. Synth. IV, 408 (1963); J. Koo, Org. Synth. V, 550 (1973).

    Google Scholar 

  59. T. F. Buckley III and H. Rapoport, J. Am. Chem. Soc. 102, 3056 (1980).

    Article  CAS  Google Scholar 

  60. H. C. Bell, J. R. Kaiman, J. T. Pinhey, and S. Sternhell, Tetrahedron Lett., 3391 (1974).

    Google Scholar 

  61. B. Chauncy and E. Geliert, Aust. J. Chem. 22, 993 (1969); R. I. Duclos, Jr., J. S. Tung, and H. Rapoport, J. Org. Chem. 49, 5243 (1984).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  63. W. Nagata, K. Okada, and T. Aoki, Synthesis, 365 (1979).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. University of Virginia, Charlottesville, Virginia, USA

    Francis A. Carey & Richard J. Sundberg

Authors
  1. Francis A. Carey
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Richard J. Sundberg
    View author publications

    You can also search for this author in PubMed Google Scholar

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 Reactions. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9797-7_11

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-9797-7_11

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-43457-0

  • Online ISBN: 978-1-4613-9797-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation