Electrophilic and nucleophilic aromatic substitution: Analogous and complementary processes

Russian Chemical Bulletin

Volumn 45, Issue 3, 1996, Pages 491-504

  Makosza M ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Carbanions; N nucleophiles; Nitroarenes; O nucleophiles; Oxidative substitution; Vicarious substitution

Indexed keywords

EID: 0038420215     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01435770     Document Type: Review

References (81)

1. P. J. Garratt, Aromaticity, J. Wiley & Sons, New York, 1986.
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.
3. 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.
4. M. V. Gorelik and L. S. Efros, Osnovy Khimii i Technologii Aromaticheskich Soedinienii [Principles of Chemistry and Technology of Aromatics Compounds], Khimia, Moscow, 1992 (in Russian).
5. C. F. Bernasconi, Chimia, 1980, 34, 1.
6. J. F. Bunnett and R. E. Zahler, Chem. Rev., 195, 49, 275.
7. J. Miller, Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968.
8. F. Terrier, Nucleophilic Aromatic Displacement, Verlag Chemie, Weinheim, 1991.
9. R. B. Davis and L. C. Pizzini, J. Org. Chem., 1960, 25, 1884.
10. E. T. McBee, E. P. Wesseler, and T. Hodgins, J. Org. Chem., 1971, 31, 2907.
11. V. von Richter, Ber., 1871, 4, 21.
12. F. Terrier, Chem. Rev., 1982, 82, 77; G. A. Artamkina, M. P. Egorov, and I. P. Beletskaya, Chem. Rev., 1982, 82, 427.
13. F. Terrier, Chem. Rev., 1982, 82, 77; G. A. Artamkina, M. P. Egorov, and I. P. Beletskaya, Chem. Rev., 1982, 82, 427.
14. E. Buncel, J. M. Dust, and F. Terrier, Chem. Rev., 1995, 95, 2261.
15. M. Ma̧kosza, Pol. J. Chem., 1992, 66, 3.
16. 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. Geterotsikl. Soedin., 1987, 1011 [Chem. Heterocycl. Compds., 1987, 23 (Engl. Transl.)].
17. 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. Geterotsikl. Soedin., 1987, 1011 [Chem. Heterocycl. Compds., 1987, 23 (Engl. Transl.)].
18. 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. Geterotsikl. Soedin., 1987, 1011 [Chem. Heterocycl. Compds., 1987, 23 (Engl. Transl.)].
19. A. Wohl, Ber., 1899, 32, 3486; French Patent 1581400 (1969), Chem. Abstr., 1970, 73, 35048; US Patent 3708545 (1969), Chem. Abstr., 1970, 73, 98593.
20. A. Wohl, Ber., 1899, 32, 3486; French Patent 1581400 (1969), Chem. Abstr., 1970, 73, 35048; US Patent 3708545 (1969), Chem. Abstr., 1970, 73, 98593.
21. A. Wohl, Ber., 1899, 32, 3486; French Patent 1581400 (1969), Chem. Abstr., 1970, 73, 35048; US Patent 3708545 (1969), Chem. Abstr., 1970, 73, 98593.
22. E. V. Malykhin, G. A. Kolesnichenko, and V. D. Shteingarts, Zh. Org. Khim., 1985, 21, 1150 [J. Org. Chem. USSR, 1985, 21 (Engl. Transl.)].
23. E. V. Malykhin, G. A. Kolesnichenko, and V. D. Shteingarts, Zh. Org. Khim., 1985, 21, 1150 [J. Org. Chem. USSR, 1985, 21 (Engl. Transl.)].
24. H. C. van der Plas and M. Woźiak. Croat. Chem. Acta, 1986, 59, 33.
25. M. Woźiak, A. Barański, and B. Szpakiewicz, Justus Liebigs Ann. Chem., 1991, 875.
26. T. J. King and C. E. Nexal, J. Chem. Soc., 1962, 367.
27. F. Kienzle, Helv. Chim. Acta, 1978, 61, 449.
28. G. Bartoli, Acc. Chem. Res., 1984, 17, 109.
29. T. V. RajanBabu, G. S. Reddy, and T. J. Fukunaga, J. Am. Chem. Soc., 1985, 107, 5473.
30. C. B. Kovalenko, G. A. Artamkina, I. P. Beletskaya, and O. A. Reutov, Metalloorg. Khim., 1988, 1, 125 [Organomet. Chem. USSR, 1988, 1 (Engl. Transl.)].
31. C. B. Kovalenko, G. A. Artamkina, I. P. Beletskaya, and O. A. Reutov, Metalloorg. Khim., 1988, 1, 125 [Organomet. Chem. USSR, 1988, 1 (Engl. Transl.)].
32. M. Hamana, G. Iwasaki, and S. Saeki, Heterocycles, 1982, 17, 177.
33. W. Danikiewicz and M. Ma̧kosza, Tetrahedron Lett., 1985, 26, 3599.
34. M. Ma̧kosza, M. Jagusztyn-Grochowska, M. Ludwikow, and M. Jawdosiuk, Tetrahedron, 1974, 30, 3723.
35. M. Ma̧kosza and M. Sypniewski, Tetrahedron, 1994, 50, 4913.
36. M. Ma̧kosza, K. Staliński, and C. Klepka, J. Chem. Soc., Chem. Commun. (in press).
37. J. P. Collman and L. S. Hegedus, Principles and Application of Organotransition Metal Chemistry, University Science Books, 1981.
38. M. F. Semmelhack, G. R. Clark, J. L. Garcia, J. J. Harrison, Y. Thebtaranonth, W. Wulff, and A. Yamashita, Tetrahedron, 1981, 37, 3957.
39. E. R. Kundig, V. Desorby, D. P. Simmons, and E. J. Wenger, J. Am. Chem. Soc., 1989, 111, 1804.
40. W. Danikiewicz and M. Ma̧kosza, J. Chem. Soc., Chem. Commun., 1985, 1792; J. Org. Chem., 1991, 56, 1285.
41. W. Danikiewicz and M. Ma̧kosza, J. Chem. Soc., Chem. Commun., 1985, 1792; J. Org. Chem., 1991, 56, 1285.
42. A. Treston, R. L. Blakeley, and B. Zerner, J. Chem. Soc., Chem. Commun., 1980, 394.
43. 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.
44. 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.
45. M. Rosenblum, J. Am. Chem. Soc., 1960, 82, 3796.
46. A. Rykowski and M. Ma̧kosza, Tetrahedron Lett., 1984, 4795.
47. C. R. McGill and A. Rappa, Adv. Heterocycl. Chem., 1988, 44, 1.
48. J. Goliński and M. Ma̧kosza, Tetrahedron Lett., 1978, 3495.
49. M. Ma̧kosza and T. Glinka, J. Org. Chem., 1983, 48, 3860.
50. M. Ma̧kosza and J. Stalewski, Justus Liebigs Ann. Chem., 1991, 605.
51. M. Ma̧kosza and J. Winiarski, Acc. Chem. Res., 1987, 20, 282; M. Ma̧kosza, Usp. Khim., 1989, 58, 1298 [Russ. Chem. Rev., 1989, 58 (Engl. Transl.)].
52. M. Ma̧kosza and J. Winiarski, Acc. Chem. Res., 1987, 20, 282; M. Ma̧kosza, Usp. Khim., 1989, 58, 1298 [Russ. Chem. Rev., 1989, 58 (Engl. Transl.)].
53. M. Ma̧kosza and J. Winiarski, Acc. Chem. Res., 1987, 20, 282; M. Ma̧kosza, Usp. Khim., 1989, 58, 1298 [Russ. Chem. Rev., 1989, 58 (Engl. Transl.)].
54. M. Ma̧kosza and Z. Owczarczyk, J. Org. Chem., 1989, 54, 5094.
55. C. C. Price and S.-T. Voong, Org. Synth. Col. Vol. III, 1955, 664.
56. 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.)].
57. 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.)].
58. A. R. Katritzky and K. S. Laurenzo, J. Org. Chem., 1988, 53, 3978.
59. M. Ma̧kosza and M. Bialecki, J. Org. Chem., 1992, 57, 4784.
60. M. Ma̧kosza and M. Sienkiewicz, J. Org Chem., 1990, 55, 4979; G. Mattersteig, W. Pritzkov, and V. Voerckel, J. Prakt. Chem., 1990, 332, 569.
61. M. Ma̧kosza and M. Sienkiewicz, J. Org Chem., 1990, 55, 4979; G. Mattersteig, W. Pritzkov, and V. Voerckel, J. Prakt. Chem., 1990, 332, 569.
62. A. Rykowski and M. Ma̧kosza, Justus Liebigs Ann. Chem., 1988, 627.
63. M. Ma̧kosza and S. Ostrowski, J. Prakt. Chem., 1988, 330, 289.
64. S. Ostrowicz, S. Baloniak, M. Ma̧kosza, and A. Rykowski, Tetrahedron Lett., 1992, 33, 4787.
65. J. Goliński, M. Ma̧kosza, and A. Rykowski, Tetrahedron Lett., 1983, 24, 3279.
66. S. Ostrowski and M. Ma̧kosza, J. Chem. Soc., Perkin Trans. 2, 1991, 1093.
67. M. Ma̧kosza, T. Glinka, S. Ostrowski, and A. Rykowski, Chem. Lett., 1987, 61.
68. S. Ostrowski and M. Ma̧kosza, Tetrahedron, 1988, 44, 1721.
69. H. C. van der Plas, Acc. Chem. Res., 1978, 11, 462.
70. D. A. de Bie, B. Geurtsen, and H. C. van der Plas, J. Org. Chem., 1985, 50, 484.
71. M. Novi, G. Guanti, F. Sancassan, and C. Dell'Erba, J. Chem. Soc., Perkin Trans. 1, 1978, 1140.
72. D. C. Morrison, J. Org. Chem., 1962, 27, 296.
73. B. J. Barnes, P. J. Newcombe, R. K. Morris, and K. Wilson, J. Chem. Soc., Chem. Commun., 1985, 1408.
74. M. Ma̧kosza and M. Niyazimbetov, Synlett, 1992, 417.
75. M. Ma̧kosza and E. Kwast, Tetrahedron, 1995, 51, 8339.
76. E. J. J. Grabowski, E. W. Tristram, R. Tull, and P. I. Pollak, Tetrahedron Lett., 1968, 5931.
77. 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. 1, 1989, 283.
78. M. Ballester, J. Riera, J. Castaner, C. Rovira, and O. Armet, Synthesis, 1986, 64.
79. L. I. Belen'kii, I. S. Poddubnyi, and M. M. Krayushkin, Tetrahedron Lett., 1995, 36, 5075.
80. H. Seeboth, Angew. Chem., 1967, 79, 329.
81. A. Jurasek, Fizikalne principy a mechanizmy organickych reakcii, Veda, Bratislava, 1989.