Preassociation, free-ion, and ion-pair pathways in the electrophilic bromination of substituted cis- and trans-stilbenes in protic solvents

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12492-12502

  Ruasse, Marie Françoise ^a   Lo Moro, Giacomo ^b   Galland, Bernard ^a   Bianchini, Roberto ^c   Chiappe, Cinzia ^b   Bellucci, Giuseppe ^d  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITY OF PISA   (Italy)

^c UNIVERSITY OF FLORENCE   (Italy)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

STILBENE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION KINETICS; ION PAIR EXTRACTION; IONIZATION; STEREOCHEMISTRY;

EID: 0031585686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9700461     Document Type: Article

References (98)

1. (a) de la Mare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd ed.; Elsevier: New York, 1982; pp 136-197.
2. (b) V'yunok, K. A.; Ginak, A. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 151.
3. (c) Schmid, G. H. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Supplement A, Vol. 3, Part 1, p 699.
4. (d) Ruasse, M. F. Adv. Phys. Org. Chem. 1993, 28, 207.
5. Brown, R. S. Acc. Chem. Res. 1997, 30, 131.
6. (a) Bellucci, G.; Bianchini, R.; Ambrosetti, R. J. Am. Chem. Soc. 1985, 107, 2464.
7. (b) Bellucci, G.; Bianchini, R.; Chiappe, C.; Lenoir, D.; Attar, A. J. Am. Chem. Soc. 1995, 117, 6243.
8. (c) Bellucci, G.; Chiappe, C.; Bianchini, R.; Lenoir, D.; Herges, R. J. Am. Chem. Soc. 1995, 117, 12001.
9. (a) Bennet, A. J.; Brown, R. S.; McClung, R. E. D.; Klobukowski, M.; Aarts, G. H. M.; Santarsiero, B. D.; Bellucci, G.; Bianchini, R. J. Am. Chem. Soc. 1991, 113, 8532.
10. (b) Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448.
11. (a) Brown R. S.; Slebocka-Tilk, H.; Bennet, A. J.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. J. Am. Chem. Soc. 1990, 112, 6310.
12. (b) Nagorski, R. W.; Slebocka-Tilk, H.; Brown, R. S. J. Am. Chem. Soc. 1994, 106, 419.
13. (c) Slebocka-Tilk, H.; Motallebi, S.; Nagorski, R. W.; Turner, P.; Brown, R. S.; McDonald, R. J. Am. Chem. Soc. 1995, 107, 8769.
14. (d) Slebocka-Tilk, H.; Gallagher, D.; Brown, R. S. J. Org. Chem. 1996, 61, 3458.
15. (a) Bellucci, G.; Chiappe, C.; Marioni, F. J. Am. Chem. Soc. 1987, 109, 515.
16. (b) Bellucci, G.; Bianchini, R.; Chiappe, C.; Marioni, F.; Spagna, R. J. Am. Chem. Soc. 1988, 110, 546.
17. (c) Bellucci, G.; Bianchini, R.; Chiappe, C.; Brown, R. S.; Slebocka-Tilk, H. J. Am. Chem. Soc. 1991, 113, 8012.
18. (d) Bellucci, G.; Chiappe, C.; Marioni, F.; Marchetti, F. J. Phys. Org. Chem. 1991, 4, 387.
19. (e) Bellucci, G.; Chiappe, C. J. Chem. Soc., Perkin Trans. 2 1997, 581.
20. (a) Ruasse, M. F.; Motallebi, S.; Galland, B. J. Am. Chem. Soc. 1991, 113, 3440.
21. (b) Ruasse, M. F.; Motallebi, S.; Galland, B.; Lomas, J. S. J. Org. Chem. 1990, 55, 2298.
22. (a) Ruasse, M. F.; Motallebi, S. J. Phys. Org. Chem. 1991, 4, 527.
23. (b) Ruasse, M. F. Acc. Chem. Res. 1990, 23, 87.
24. (a) Ruasse, M. F.; Zhang, B. L. J. Org. Chem. 1984, 49, 3207.
25. (b) Ruasse, M. F.; Lefebvre, E. J. Org. Chem. 1984, 49, 3210.
26. (a) Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1.
27. (b) Raber, D. J.; Neal, W. C.; Dukes, M. D.; Harris, J. M.; Mount, D. L. J. Am. Chem. Soc. 1978, 100, 8137.
28. (c) Harris, J. M.; Mount, D. L.; Smith, M. R.; Neal, W. C.; Dukes, M. D.; Raber, D. J. J. Am. Chem. Soc. 1978, 100, 8147.
29. (d) Bentley, T. W.; Bowen, C. T.; Morten, D. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 5466.
30. (a) Ridd, J. H. Adv. Phys. Org. Chem. 1979, 16, 1.
31. (b) Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
32. (c) Cox, M. M.; Jencks, W. P. J. Am. Chem. Soc. 1981, 103, 572.
33. (d) Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345.
34. (e) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1373.
35. (f) Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361.
36. (g) Amyes, T. L.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7888.
37. (h) Eldin, S.; Jencks, W. P. J. Am. Chem. Soc. 1995, 117, 4851.
38. Ambrosetti, R.; Bellucci, G.; Bianchini, R.; Fontana, E.; Ricci, D. J. Phys. Chem. 1994, 98, 1620.
39. (a) Walker, I. K.; Robertson, P. W. J. Chem. Soc. 1939, 1315.
40. (b) Yates, K.; McDonald, R. S.; Shapiro, S. A. J. Org. Chem. 1973, 38, 2460.
41. Ruasse, M. F.; Aubard, J.; Galland, B.; Adenier, A. J. Phys. Chem. 1986, 90, 4382.
42. (a) Bartlett, P. D.; Tarbell, D. S. J. Am. Chem. Soc. 1936, 58, 466.
43. (b) Dubois, J. E.; Bienvenue-Goëtz, E. Bull. Soc. Chim. Fr. 1968, 2089.
44. (c) Dubois, J. E.; Huynh, X. Q. Tetrahedron Lett. 1971, 3369.
45. (a) Grunwald, E.; Winstein, S. J. Am. Chem. Soc. 1948, 70, 846.
46. (b) Winstein, S.; Fainberg, A. H.; Grunwald, E. J. Am. Chem. Soc. 1957, 79, 4146.
47. (c) Grunwald, E. Chemtech 1984, 14, 698.
48. (a) Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 574.
49. (b) Bentley, T. W.; Llewellyn, G. Prog. Phys. Chem. 1990, 17, 121.
50. (a) Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1976, 98, 7667.
51. (b) Bentley; T. W. In Nucleophilicity; Harris, J. M., McManus, S. P., Eds; American Chemical Society: Washington, DC, 1987; pp 255-268.
52. Garnier, F.; Donnay, R. H.; Dubois, J. E. J. Chem. Soc., Chem. Commun. 1971, 829.
53. Fieser, L. F. J. Chem. Ed. 1954, 31, 291.
54. The terms "erythro" and "threo" are not strictly applicable to these diastereoisomers. They are used here as a convenient way of describing the stereochemistry of dibromide and mixed adduct formation.
55. Dalton, D. L.; Dutta, P.; Jones, D. C. J. Am. Chem. Soc. 1968, 90, 5498.
56. (a) Attempts to brominate p,p′-dimethoxystilbenes in methanol yielded 1,2-dimethoxy-1,2-di(p-methoxyphenyl)ethane arising from the solvolysis of the first formed methoxybromo adduct.
57. (b) Ruasse, M. F.; Argile, A. J. Org. Chem. 1983, 48, 202.
58. Jackman, L. M.; Sternhell, S. Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon Press: Oxford, 1969; p 291.
59. Rolston, J. H.; Yates, K. J. Am. Chem. Soc. 1969, 91, 1469.
60. Walling, C.; Rieger, A. L.; Tanner, D. D. J. Am. Chem. Soc. 1963, 85, 3129.
61. (a) Ruasse, M. F.; Dubois, J. E. J. Org. Chem. 1972, 37, 1770.
62. (b) Ruasse, M. F.; Dubois, J. E. J. Org. Chem. 1973, 38, 473; 1974, 39, 2441.
63. (b) Ruasse, M. F.; Dubois, J. E. J. Org. Chem. 1973, 38, 473; 1974, 39, 2441.
64. 28 see footnote 14 in ref 27a.
65. Tsuno, Y.; Fujio, H. Chem. Soc. Rev. 1996, 25, 129.
66. Cox, B. G.; Maskill, H. J. Chem. Soc., Trans. Perkin 2 1983, 1901.
67. (a) Richard, J. P.; Amyes, T. L.; Vontor, T. J. Am. Chem. Soc. 1991, 113, 5871.
68. (b) Toteva, M. H.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 11434.
69. Nagorski, R. W.; Brown, R. S. J. Am. Chem. Soc. 1992, 114, 7773.
70. Ruasse, M. F.; Argile, A.; Dubois, J. E. J. Am. Chem. Soc. 1978, 100, 7645.
71. (a) Dubois, J. E.; Chrétien, J. R. J. Am. Chem. Soc. 1978, 100, 3506.
72. (b) Ruasse, M. F.; Coudert, D.; Chrétien, J. R. J. Org. Chem. 1993, 58, 1917.
73. (c) Ruasse, M. F.; Argile, A. J. Org. Chem. 1983, 48, 202.
74. (a) Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455.
75. (b) McClelland, R. A.; Kanagasabapathy, V. M.; Steenken, S. J. Am. Chem. Soc. 1988, 110, 6913.
76. (c) McClelland, R. A.; Chan, C.; Cozens, F.; Modro, A.; Steenken, S. Angew. Chem. Int. Ed. Engl. 1991, 30, 1337.
77. (d) Das, P. K. Chem. Rev. 1993, 93, 119.
78. (e) McClelland, R. A. In Organic Reactivity: Physical and Biological Aspects; Golding, B. T., Griffin, R. J., Maskill, H., Eds; The Royal Society of Chemistry: Cambridge, 1995; p 301.
79. Paradisi, C.; Bunnett, J. F. J. Am. Chem. Soc. 1985, 107, 8223.
80. - capture of free ions 5 is excluded because of the very low concentration of bromide ions resulting from the dissociation of the ion pair.
81. It should be noted also that dibromide is obtained with a stereoselectivity better than that of MA, showing that the lifetime of the free ion is longer than that of the ion pair.
82. (a) Sneen, R. A. Acc. Chem. Res. 1973, 6, 46.
83. (b) Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. In Ions and Ion-Pairs in Organic Reactions; Szwarc M., Ed.; Wiley: New York, 1974; Vol. 2, p 247.
84. -1 range, according to preliminary measurements of lifetimes of stilbene bromination intermediates (Chiappe, C.; Lo Moro, G.; Ruasse, M. F, unpublished results).
85. Bellucci, G.; Chiappe, C. J. Phys. Org. Chem., in press.
86. +-MeOH reaction. This primary effect would superimpose to the KSIE on the ionization step resulting in the observed increase in the experimental value.
87. Return in the absence of crowding was also supported by results on solvolysis of β-bromotriflates in the presence of bromide ions. Zheng, C. Y.; Slebocka-Tilk, H.; Nagorski, R. W.; Alvarado, L.; Brown, R. S. J. Org. Chem. 1993, 58, 2122.
88. (a) Poirier, R. A.; Mezey, P. G.; Yates, K.; Cszimadia, I. G. J. Mol. Struct. 1983, 94, 137.
89. (b) Galland, B.; Evleth, E.; Ruasse, M. F. J. Chem. Soc., Chem. Commun. 1990, 898.
90. (c) Hamilton, T. P.; Schaefer, H. F. J. Am. Chem. Soc. 1990, 112, 8260.
91. (d) Klobukowski, M.; Brown, R. S. J. Org. Chem. 1994, 59, 7156.
92. (e) Cossi, M.; Persico, M.; Tomasi, J. J. Am. Chem. Soc. 1994, 116, 5373.
93. (a) Buckles, R. E.; Bader, J. N.; Thurmaier, R. J. J. Org. Chem. 1962, 27, 4523.
94. (b) Heublein, G. J. Prakt. Chem. 1966, 303, 84.
95. De Young, S.; Ehrlich, S. J.; Berliner, E. J. Am. Chem. Soc. 1977, 99, 290.
96. (b) Ehrlich, S. J.; Berliner, E. J. Am. Chem. Soc. 1978, 100, 1525.
97. (c) De Young, S.; Berliner, E.; J. Org. Chem. 1979, 44, 1088.
98. Novotny, J.; Collins, C. H.; Starks, F. W. J. Pharm. Sci. 1973, 62, 610.