Aromatic Substitution by the SRN1 Mechanism

Accounts of Chemical Research

Volumn 11, Issue 11, 1978, Pages 413-420

  Bunnett, Joseph F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26644442183     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar50131a003     Document Type: Article

References (65)

1. E. Mitscherlich, Ann. Pharm., 9,39 (1834);
2. Ann. Phys., 31,625 (1835).
3. J. K. Kim and J. F. Bunnett, J. Am. Chem. Soc., 92,7463,7464 (1970).
4. N. Kornblum, R. E. Michel, and R. C. Kerber, J. Am. Chem. Soc., 88, 5662 (1966);
5. before 1966, R. C. Kerber, G. W. Urry, and N. Kornblum (J. Am. Chem. Soc., 86, 3904 (1964); 87, 4520 (1965))
6. F. M. Beringer, S. A. Galton, and S. J. Huang (N. Kornblum (J. Am. Chem. Soc., 84,2819 (1962)
7. G. A. Russell and W. C. Danen, J. Am. Chem. Soc., 88, 5663 (1966); 90, 347 (1968).
8. N. Kornblum, Angew. Chem., 87, 797 (1975);
9. Angew. Chem., Int. Ed. Engl., 14, 734 (1975).
10. L. Nadjo and J. M. Saveant, J. Electroanal. Chem., 30, 41 (1971).
11. K. Alwair and J. Grimshaw, J. Chem. Soc., Perkin Trans. 2, 1150 (1973).
12. A. L. J. Beckwith and R. O. C. Norman, J. Chem. Soc. B, 403 (1969).
13. D. E. Bartak, W. C. Danen, and M. D. Hawley, J. Org. Chem., 35, 1206 (1970).
14. L. M. Dorfman, Acc. Chem. Res., 3, 224 (1970).
15. J. K. Kim, Ph.D. Dissertation, University of California, Santa Cruz, June 1970.
16. J. F. Bunnett and R. E. Zahler, Chem. Rev., 49, 273 (1951).
17. J. F. Bunnett, Q. Rev. Chem. Soc., 12, 1 (1958).
18. R. A. Rossi and J. F. Bunnett, J. Org. Chem., 37, 3570 (1972).
19. R. A. Rossi and J. F. Bunnett, J. Am. Chem. Soc., 94, 683 (1972).
20. R. A. Rossi and J. F. Bunnett, J. Org. Chem., 38, 3020 (1973).
21. J. F. Bunnett and B. F. Gloor, J. Org. Chem., 38, 4156 (1973).
22. R. A. Rossi, R. H. de Rossi, and A. F. Lopez, J. Am. Chem. Soc., 98, 1252 (1976).
23. R. A. Rossi and J. F. Bunnett, J. Org. Chem., 38, 1407 (1973).
24. J. Pinson and J.-M. Saveant, J. Chem. Soc., Chem. Commun., 934 (1974);
25. J. Am. Chem. Soc., 100, 1506 (1978).
26. R. G. Scamehorn and J. F. Bunnett, J. Org. Chem., 42,1449 (1977).
27. J. F. Bunnett and J. E. Swartz, Abstracts, 175th National Meeting of the American Chemical Society, Anaheim, Calif., March 1978, ORGN 30.
28. R. A. Rossi and J. F. Bunnett, J. Am. Chem. Soc., 96,112 (1974).
29. H.-J. Opgenorth and C. Riichardt, Justus Liebigs Ann. Chem., 1333 (1974).
30. N. A. Porter, L. J. Marnett, C. H. Lochmuller, G. L. Closs, and M. Shobataki, J. Am. Chem. Soc., 94, 3664 (1972).
31. P. R. Singh and R. Kumar, Aust. J. Chem., 25, 2133 (1972).
32. J. F. Bunnett and J. E. Sundberg, Chem. Pharm. Bull., 23, 2620 (1975).
33. R. A. Rossi, R. H. de Rossi, and A. F. Lopez, J. Org. Chem., 41, 3371 (1976).
34. J. F. Bunnett and B. F. Gloor, J. Org. Chem., 39, 382 (1974).
35. J. F. Bunnett and X. Creary, J. Org. Chem., 39, 3173 (1974).
36. J. F. Bunnett and X. Creary, J. Org. Chem., 39, 3612 (1974).
37. J. F. Wolfe, J. C. Greene, and T. Hudlicky, J. Org. Chem., 37, 3199 (1972).
38. J. V. Hay, T. Hudlicky, and J. F. Wolfe, J. Am. Chem. Soc., 97, 374 (1975).
39. J. V. Hay and J. F. Wolfe, J. Am. Chem. Soc., 97, 3702 (1975).
40. A. P. Komin and J. F. Wolfe, J. Org. Chem., 42, 2481 (1977).
41. J. A. Zoltewicz and T. M. Oestreich, J. Am. Chem. Soc., 95, 6863 (1973).
42. D. A. de Bie, H. C. van der Plas, and B. Geurtsen, J. Chem. Soc., Perkin Trans. 1, 1363 (1974).
43. J. F. Bunnett and B. F. Gloor, Heterocycles, 5, 377 (1976).
44. J. F. Bunnett, X. Creary, and J. E. Sundberg, J. Org. Chem., 41, 1707 (1976).
45. A. B. Pierini and R. A. Rossi, J. Organometal. Chem., 144, C12 (1978).
46. J. F. Bunnett and J. E. Sundberg, J. Org. Chem., 41,1702 (1976).
47. M. F. Semmelhack and T. M. Bargar, J. Org. Chem., 42,1481 (1977).
48. J. F. Bunnett and X. Creary, unpublished work.
49. J. F. Bunnett and R. H. Weiss, “Organic Syntheses”, John Wiley, New York, N.Y., in press.
50. J. F. Bunnett and J. E. Swartz, unpublished work.
51. J. F. Bunnett and X. Creary, J. Org. Chem., 39, 3611 (1974).
52. J. F. Bunnett and X. Creary, J. Org. Chem., 40, 3740 (1975).
53. M. F. Semmelhack, B. P. Chong, R. D. Stauffer, T. D. Rogerson, A. Chong, and L. D. Jones, J. Am. Chem. Soc., 97, 2507 (1975).
54. J. F. Bunnett, R. G. Scamehorn, and R. P. Traber, J. Org. Chem., 41, 3677 (1976).
55. S. Hoz and J. F. Bunnett, J. Am. Chem. Soc., 99, 4690 (1977).
56. J. F. Bunnett and R. P. Traber, J. Org. Chem., 43, 1867 (1978).
57. J. F. Bunnett and S. J. Shafer, J. Org. Chem., 43, 1873 (1978).
58. J. F. Bunnett and S. J. Shafer, J. Org. Chem., 43, 1877 (1978).
59. L. D. Freedman and H. H. Jaffe, J. Am. Chem. Soc., 77, 920 (1955).
60. H. H. Szmant and G. Suld, J. Am. Chem. Soc., 78, 3400 (1956).
61. R. A. Rossi, R. H. de Rossi, and A. F. Lopez, J. Org. Chem., 41, 3367 (1976).
62. R. G. Scamehorn and J. F. Bunnett, Abstracts, 4th IUPAC Conference on Physical Organic Chemistry, York, England, Sept 1978.
63. A. M. Aguiar, H. J. Greenberg, and K. E. Rubenstein, J. Org. Chem., 28, 2091 (1963).
64. J. F. Bunnett and F. J. Kearley, Jr., J. Org. Chem., 36,184 (1971).
65. K. R. Wursthorn, H. G. Kuivila, and G. F. Smith, J. Am. Chem. Soc., 100, 2779 (1978).