Skip to main content
SpringerLink
Log in

Electrophilic and nucleophilic aromatic substitution: Analogous and complementary processes

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Analysis of many variants of nucleophilic aromatic substitution of hydrogen proceeding according to an addition—elimination pattern reveals that this is the major reaction pathway, whereas nucleophilic replacement of halogen or another nucleofugal group is the secondary process, i.e.,ipso-substitution. In this respect electrophilic and nucleophilic aromatic substitution can be considered as analogous processes.

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

References

  1. P. J. Garratt,Aromaticity, J. Wiley & Sons, New York, 1986.

    Google Scholar 

  2. F. A. Carey and R. J. Sundberg,Advanced Organic Chemistry, Third Ed., Plenum Press, New York, 1990.; J. March,Advanced Organic Chemistry, Fourth Ed., J. Wiley & Sons, New York, 1992.

    Google Scholar 

  3. M. V. Gorelik and L. S. Efros,Osnovy Khimii i Technology Aromaticheskich Soedinienii [Principles of Chemistry and Technology of Aromatics Compounds], Khimia, Moscow, 1992 (in Russian).

    Google Scholar 

  4. C. F. Bemasconi,Chimia, 1980,34, 1.

    Google Scholar 

  5. J. F. Bunnett and R. E. Zahler,Chem. Rev., 195,49, 275.

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

    Google Scholar 

  7. F. Terrier,Nucleophilic Aromatic Displacement, Verlag Chemie, Weinheim, 1991.

    Google Scholar 

  8. R. B. Davis and L. C. Pizzini,J. Org. Chem., 1960,25, 1884.

    Google Scholar 

  9. E. T. McBee, E. P. Wesseler, and T. Hodgins,J. Org. Chem., 1971,31, 2907.

    Google Scholar 

  10. V. von Richter,Ber., 1871,4, 21.

    Google Scholar 

  11. F. Terrier,Chem. Rev., 1982,82, 77; G. A. Artamkina, M. P. Egorov, and I. P. Beletskaya,Chem. Rev., 1982,82, 427.

    Google Scholar 

  12. E. Buncel, J. M. Dust, and F. Terrier,Chem. Rev., 1995,95, 2261.

    Google Scholar 

  13. M. Mąkosza,Pol. J. Chem., 1992,66, 3.

    Google Scholar 

  14. O. N. Chupakhin, V. N. Charushin, and H. C. van der Plas,Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, San Diego, 1994; H. van der Plas,Khim. Gererotsikl. Soedin.,1987, 1011 [Chem. Heterocycl. Compds., 1987,23 (Engt. Transl.)].

    Google Scholar 

  15. A. Wohl,Ber., 1899,32, 3486; French Patent 1581400 (1969),Chem. Abstr., 1970,73, 35048; US Patent 3708545 (1969),Chem. Abstr., 1970,73, 98593.

    Google Scholar 

  16. E. V. Malykhin, G. A. Kolesnichenko, and V. D. Shteingarts,Zh. Org. Khim., 1985,21, 1150 [J. Org. Chem. USSR, 1985,21 (Engt. Transl.)].

    Google Scholar 

  17. H. C. van der Plas and M. Woźiak.Croat. Chem. Acta, 1986,59, 33.

    Google Scholar 

  18. M. Woźiak, A. Barański, and B. Szpakiewicz,Justus Liebigs Ann. Chem., 1991, 875.

  19. T. J. King and C. E. Nexal,J. Chem. Soc., 1962, 367.

  20. F Kienzle,Helv. Chim. Acta, 1978,61, 449.

    Google Scholar 

  21. G. Bartoli,Acc. Chem. Res., 1984,17, 109.

    Google Scholar 

  22. T. V. RajanBabu, G. S. Reddy, and T. J. Fukunaga,J. Am. Chem. Sac., 1985,147, 5473.

    Google Scholar 

  23. C. B. Kovalenko, G. A. Attarnkina, I. P. Beletskaya, and O. A. Reutov,Metalloorg. Khim., 1988,1, 125[(Organomet. Chem. USSR, 1988,1 (Engl. Transt.)].

    Google Scholar 

  24. M. Hamana, G. Iwasaki, and S. Saeki,Heterocycles, 1982,17, 177.

    Google Scholar 

  25. W. Danikiewicz and M. Mąkosza,Tetrahedron Lett., 1985,26, 3599.

    Google Scholar 

  26. M. Mąkosza, M. Jagusztyn-Grochowska, M. Ludwikow, and M. Jawdosiuk,Tetrahedron, 1974,30, 3723.

    Google Scholar 

  27. M. Mąkosza and M. Sypniewski,Tetrahedron, 1994,50, 4913.

    Google Scholar 

  28. M. Mąkosza, K. Stalinski, and C. Klepka,J. Chem. Soc., Chem. Commun. (in press).

  29. I. P. Collman and L. S. Hegedus,Principles and Application of Organotransition Metal Chemistry, University Science Books, 1981.

  30. M. F. Semmelhack, G. R. Clark, J. L. Garcia, J. J. Harrison, Y. Thebtaranonth, W. Wulff, and A. Yamashita,Tetrahedron, 1981,37, 3957.

    Google Scholar 

  31. E. R. Kundig, V. Desorby, D. P. Simmons, and E. J. Wenger,J. Am. Chem. Soc., 1989,111, 1804.

    Google Scholar 

  32. W. Danikiewicz and M. Mąkosza,J. Chem. Soc., Chem. Commun., 1985, 1792;J. Org. Chem., 1991,56, 1285.

    Google Scholar 

  33. A. Treston, R. L. Blakeley, and B. Zemer,J. Chem. Soc., Chem. Commun., 1980, 394.

  34. Y. Tomioka, Mochiike, J. Himeno, and M. Yamazaki,Chem. Pharm. Bull., 1981,29, 1286; Y. Tomioka, K. Ohkubo, and M. Yamazaki,ibid., 1985,33, 1360.

    Google Scholar 

  35. M. Rosenblum,J. Am. Chem. Soc., 1960,82, 3796.

    Google Scholar 

  36. A. Rykowski and M. Mąkosza,Tetrahedron Lett., 1984, 4795.

  37. C. R. McGill and A. Rappa,Adv. Heterocycl. Chem., 1988,44, 1.

    Google Scholar 

  38. J. Goliński and M. Mąkosza,Tetrahedron Lett., 1978, 3495.

  39. M. Mąkosza and T. Glinka,J. Org. Chem., 1983,48, 3860.

    Google Scholar 

  40. M. Mąkosza and J. Stalewski,Justus Liebigs Ann. Chem., 1991, 605.

  41. M. Mąkosza and J. Winiarski,Acc. Chem. Res., 1987,20, 282; M. Mąkosza,Usp. Khim., 1989,58, 1298 [Russ. Chem. Rev., 1989, 58 (Engl. Transl.)].

    Google Scholar 

  42. M. Mąkosza and Z. Owczarczyk,J. Org. Chem., 1989,54, 5094.

    Google Scholar 

  43. C. C. Price and S.-T. Voong,Org. Synth. Col. Vol. III, 1955, 664.

    Google Scholar 

  44. S. S. Gitis, A. I. Glaz, B. B. Grigoriev, A. Y. Kaminsky, A. S. Martynienko, and P. I. Saukov,Zh. Org. Khim., 1967,3, 1617 [J. Org. Chem. USSR, 1967, 3 (Engl. Transl.)].

    Google Scholar 

  45. A. R. Katritzky and K. S. Laurenzo,J. Org. Chem., 1988,53, 3978.

    Google Scholar 

  46. M. Mąkosza and M. Bialecki,J. Org. Chem., 1992,57, 4784.

    Google Scholar 

  47. M. Mąkosza and M. Sienkiewicz,J. Org. Chem., 1990,55, 4979; G. Mattersteig, W. Pritzkov, and V. Voerckel,J. Prakt. Chem., 1990,332, 569.

    Google Scholar 

  48. A. Rykowski and M. M4kosza,Justus Liebigs Ann. Chem., 1988, 627.

  49. M. Mąkosza and S. Ostrowski,J. Prakt. Chem., 1988,330, 289.

    Google Scholar 

  50. S. Ostrowicz, S. Baloniak, M. Mąkosza, and A. Rykowski,Tetrahedron Lett., 1992,33, 4787.

    Google Scholar 

  51. J. Goliński, M. Mąkosza, and A. Rykowski,Tetrahedron Lett., 1983,24, 3279.

    Google Scholar 

  52. S. Ostrowski and M. M4kosza, J. Chem. Soc.,Perkin Trans. 2, 1991, 1093.

  53. M. Mąkosza, T. Glinka, S. Ostrowski, and A. Rykowski,Chem. Len., 1987, 61.

  54. S. Ostrowski and M. Mąkosza,Tetrahedron, 1988,44, 1721.

    Google Scholar 

  55. H. C. van der Plas,Acc. Chem. Res., 1978,11, 462.

    Google Scholar 

  56. D. A. de Bie, B. Geurtsen, and H. C. van der Plas,J. Org. Chem., 1985,50, 484.

    Google Scholar 

  57. M. Novi, G. Guanti, F. Sancassan, and C. Dell'Erba,J. Chem. Soc., Perkin Trans. I, 1978, 1140.

  58. D. C. Morrison,J. Org. Chem., 1962,27, 296.

    Google Scholar 

  59. B. J. Barnes, P. J. Newcombe, R. K. Norris, and K. Wilson,J. Chem. Soc., Chem. Commun., 1985, 1408.

  60. M. Mąkosza and M. Niyazimbetov,Synlett, 1992, 417.

  61. M. Mąkosza and E. Kwast,Tetrahedron, 1995,51, 8339.

    Google Scholar 

  62. E. I. I. Grabowski, E. W. Tristram, R. Tull, and P. I. Pollak,Tetrahedron Lett., 1968, 5931.

  63. R. S. Dainter, T. Jackson, A. H. H. Omar, H. Suschitzky, B. J. Wakefield, N. Hughes, A. J. Nelson, and G. Varvounis,J. Chem. Soc., Perkin Trans. I, 1989, 283.

  64. M. Bafester, J. Riera, J. Castaner, C. Rovira, and O. Annet,Synthesis,1986, 64.

  65. L. I. Belen'kii, I. S. Poddubnyi, and M. M. Krayushkin,Tetrahedron Lett., 1995,36, 5075.

    Google Scholar 

  66. H. Seeboth,Angew. Chem., 1967,79, 329.

    Google Scholar 

  67. A. Jurasek,Fzikalne principy a mechanizmy organickych reakcii, Veda, Bratislava, 1989.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland

    M. Mąkosza

Authors
  1. M. Mąkosza
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

This account is published in connection awarding Prof. M. Mgkosza the degree ofDoctor Honoris causa by the Russian Academy of Sciences for his investigations in the fields of physical organic chemistry and fine organic synthesis.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3. pp. 531–544, March, 1996.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mąkosza, M. Electrophilic and nucleophilic aromatic substitution: Analogous and complementary processes. Russ Chem Bull 45, 491–504 (1996). https://doi.org/10.1007/BF01435770

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01435770

Key words

Search

Navigation