The anomalous reactivity of fluorobenzene in electrophilic aromatic substitution and related phenomena

Journal of Chemical Education

Volumn 80, Issue 6, 2003, Pages 679-690

  Rosenthal, Joel ^a,b   Schuster, David I ^a  

^a NEW YORK UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONS; FLUORINE COMPOUNDS; IONS; RESONANCE; SUBSTITUTION REACTIONS;

FLUOROBENZENE;

BENZENE;

EID: 0037850958     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed080p679     Document Type: Article

References (50)

1. Brown, B.; Foote, C. S. Organic Chemistry, 2nd ed.; Saunders College Publishing: New York, 1998.
2. Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed.; Macmillan Publishing Company: New York, 1992.
3. Vollhardt, K. P. C. Organic Chemistry, 1st ed.; W. H. Freeman and Company: New York, 1987.
4. Jones, Maitland, Jr. Organic Chemistry; W. W. Norton and Company: New York, 2000.
5. Taylor, R. Electrophilic Aromatic Substitution; J. Wiley: Chichester, West Sussex, England; New York, 1990.
6. McMurry, J. Organic Chemistry, 4th ed.; Brooks/Cole Publishing Company: Albany, 1996.
7. Hoggett, J. G. Nitration and Aromatic Reactivity; Cambridge University Press: London, 1971.
8. Gould, E. S. Mechanism and Structure in Organic Chemistry, 1st ed.; Holt, Rinehart and Winston Inc.: New York, 1959.
9. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, 1969.
10. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A: Structure and Mechanisms, 3rd ed.; Plenum Press: New York, 1990.
11. Eaborn, C.; Taylor, R. J. Chem. Soc. 1961, 2388-2393.
12. Rys, P.; Skrabal, R.; Zollinger, H. Angew. Chem., Int. Ed. 1972, 11, 874.
13. Wiberg, K. B.; Rablen, P. R. J. Org. Chem. 1998, 63, 3722-3730.
14. Wiberg, K. B. J. Chem. Educ. 1996, 73, 1089-1095
15. Wiberg, K. B.; Marquez, M. J. Am. Chem. Soc. 1998, 120, 2932-2938.
16. Jorgensen, W. L.; Cournoyer, M. E. J. Am. Chem. Soc. 1978, 100, 5278-5285.
17. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
18. Okamoto, Y.; Brown, H. C. J. Org. Chem. 1957, 22, 485-494.
19. Streitwieser, A., Jr. Solvolytic Displacement Reactions, 1st ed.; McGraw-Hill Book Company, Inc.: New York, 1962.
20. Sheppard, W. A.; Sharts, C. M. Organic Fluorine Chemistry; W. A. Benjamin: New York, 1969.
21. Baker, J. W.; Hopkins, H. B. J. Chem. Soc. 1949, 1084.
22. Fieser, L. F.; Fieser, M. Textbook of Organic Chemistry; Heath: Boston, 1950.
23. Wheland, G. W. Resonance in Organic Chemistry; John Wiley & Sons: New York, 1955.
24. Bures, M. G.; Roos-Kozel, B. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 50, 4490.
25. Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry, 1st ed.; Brooks/Cole Publishing Company: New York, 1998.
26. Ingold, C. K.; Shaw, F. Ruth J. Chem. Soc. 1931, 1959.
27. Ingold, C. K.; Shaw, F. Ruth J. Chem. Soc. 1927, 2918-2926.
28. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, New York, 1960.
29. Wheland, G. W. J. Am. Chem. Soc. 1942, 64, 900.
30. Stock, L. M. Aromatic Substitution Reactions; Prentice-Hall: Englewood Cliffs, NJ, 1968.
31. Leffler, J. E. Science 1953, 117, 340.
32. Hammond, G. S. J. Am. Chem. Soc. 1955, 77 334.
33. Jones, R. A. Y. Physical and Mechanistic Organic Chemistry, 2nd ed.; Cambridge University Press: Cambridge, 1984.
34. Brown, H. C.; Marino, G. J. Am. Chem. Soc. 1959, 81, 3308.
35. Olah, G. A.; Kuhn, S. J.; Flood, S. H.; Hardie, B. A. J. Am. Chem. Soc. 1964, 86, 2203.
36. Olah, G. A.; Moffatt, M. E.; Kuhn, S. J.; Hardie, B. A. J. Am. Chem. Soc. 1964, 86, 2198.
37. Stock, L. M. J. Am. Chem. Soc. 1959, 81, 3210.
38. Gritsan, N. P.; Gudmundsdottir, A. D.; Tigelaar, D.; Shu, S.; Karney, W. L.; Hadad, C. M.; Platz, M. S. J. Am. Chem. Soc. 2001, 123, 1951-1962.
39. Perrin, D.D. Pure Appl. Chem. 1965, 37, 1-473.
40. Kortum, G.; Vogel, W.; Andrussow, K. Pure Appl. Chem. 1961, 33, 190-536.
41. Melander, L. In The Transition State; The Chemical Society: London, 1962; Vol. 16, p 208.
42. Gandler, J. R.; Setiarahardjo, I. U.; Tufon, C.; Chen, C. J. Org. Chem. 1992, 57, 4169-4173.
43. Bunnett, J. F.; Garbisch E. W., Jr.; Pruitt, K. J. Am. Chem. Soc. 1957, 79, 385-391.
44. Poupko, R.; Zimmermann, H.; Müller, K.; Luz, Z. J. Am. Chem. Soc. 1996, 118, 7995-5005.
45. Oth, J. F.; Merenyi, R.; Röttele, H.; Schröder, G. Tetrahedron Lett. 1968, 3941-3946.
46. Poupko, R.; Zimmermann, H.; Luz, Z. J. Am. Chem. Soc. 1984, 106, 5391-5394.
47. Roberts, J. D.; Chambers, V. J. Am. Chem. Soc. 1951, 73, 5034-5040.
48. Dolbier, J.; William, R.; Fielder, J.; Thomas, H. J. Am. Chem. Soc. 1978, 100, 5577-5578.
49. Weiss, H. M. J. Chem. Educ. 1996, 73, 1082.
50. Weiss, H. M. J. Chem. Educ. 1993, 70, 873.