Synthesis and dynamic properties of cycloheptatrienyl(dipropyl)borane. Equilibrium with 7-dipropylborylnorcaradiene

Journal of the American Chemical Society

Volumn 120, Issue 5, 1998, Pages 1034-1043

  Gridnev, Ilya D ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; DEUTERIUM; METHYL GROUP; PROTON;

ARTICLE; DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROPRIOCEPTION; SYNTHESIS; TEMPERATURE; THERMODYNAMICS;

EID: 0032507030     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9724699     Document Type: Article

References (101)

1. (a) Larrabee, R. B. J. Am. Chem. Soc. 1971, 93, 1510.
2. (b) Curtis, M. D.; Fink, R. J. Organomet. Chem. 1972, 38, 299.
3. (c) Mann, B. E.; Taylor, B. F.; Taylor, N. A.; Wood, R. Ibid. 1978, 162, 137.
4. (d) Spangler, C. W. Chem. Rev. (Washington, D.C.) 1976, 76, 187.
5. (e) Ashe, A. J., III J. Org. Chem. 1972, 37, 2053.
6. (f) Larrabee, R. B. J. Organomet. Chem. 1974, 74, 313.
7. (g) Shono, T.; Maekawa, H.; Nozoe, T.; Kashimura, S. Tetrahedron Lett. 1990, 31, 895.
8. (h) Heinekey, D. M.; Graham, W. A. G. J. Am. Chem. Soc. 1979, 101, 6115.
9. (i) Heinekey, D. M.; Graham, W. A. G. Ibid. 1982, 104.
10. (j) Dushenko, G. A.; Mikhailov, I. E.; Zschunke, A.; Hakam, N.; Mügge, C.; Minkin, V. I. MendeleeV Commun. 1995, 133.
11. (k) Dushenko, G. A.; Mikhailov, I. E.; Zschunke, A.; Hakam, N.; Mügge, C.; Minkin, V. I. MendeleeV Commun. 1997, 50.
12. (a) Benn, R.; Cibura, K.; Hoffmann, P.; Jonas, K.; Rufinska, A. Organometallics 1985, 4, 2214.
13. (b) ShingMan, L. K. K.; Reuvers, J. G. A.; Takats, J.; Deganello, G. Organometallics 1983, 2, 28.
14. (c) Davies, E. S.; Whitely, M. W. J. Organomet. Chem. 1996, 519, 216.
15. Gridnev, I. D.; Tok, O. L.; Gurskii, M. E.; Bubnov, Yu. N. Chem. Eur. J. 1996, 2, 1483.
16. (a) For reviews, see: (a) Maier, G. Angew. Chem. 1967, 79, 446.
17. (b) Vogel, E. Pure Appl. Chem. 1969, 20, 237.
18. le (c) Noble, W. J. Highlights of Organic Chemistry; Dekker: New York, 1974; p 402.
19. (d) Liebman, J. F. Chem. Rev. 1989, 89, 1225.
20. (e) Okamura, W. H.; Delera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 699.
21. Willstätter, R. Liebigs Ann. Chem. 1901, 317, 204.
22. (a) Darms, R.; Threlfall, T.; Pesaro, M.; Eschenmoser, A. Helv. Chim. Acta 1963, 46, 1893.
23. (b) Vogel, E.; Wiedemann, W.; Kiefer, H.; Harrison, V. F. Tetrahedron Lett. 1963, 673.
24. (c) Ciganek, E. J. Am. Chem. Soc. 1967, 89, 1454.
25. (d) Mukai, T.; Kubota, H.; Toda, T. Tetrahedron Lett. 1967, 3581.
26. (e) Schönleber, D. Angew. Chem. 1969, 81, 83.
27. (f) Jones, M., Jr. Ibid. 1969, 81, 87.
28. (a) Knox, L. H.; Velarde, E.; Cross, A. D. J. Am. Chem. Soc. 1963, 85, 5, 2533.
29. (b) Knox, L. H.; Velarde, E.; Cross, A. D. ibid. 1965, 87, 3727.
30. (c) Lambert, J. B.; Durham, L. J.; Lepoutere, P.; Roberts, J. D. Ibid. 1965, 87, 3896.
31. (d) Vogel, E.; Maier, W.; Eimer, J. Tetrahedron Lett. 1966, 655.
32. (e) Gale, D. M.; Middleton, W. J.; Krespan, C. G. J. Am. Chem. Soc. 1966, 88, 3617.
33. (f) Bushweller, C. H.; Sharpe, M.; Weininger, S. J. Tetrahedron Lett. 1970, 453.
34. (a) Ciganek, E. J. Am. Chem. Soc. 1965, 87, 1149.
35. (b) Görlitz, M.; Günter, H. Tetrahedron 1969, 4467.
36. (c) Hall, G. E.; Roberts, J. D. J. Am. Chem. Soc. 1971, 93, 2203.
37. (d) Ciganek, E. Ibid. 1971, 93, 2207.
38. (a) Daub, J.; Betz, W. Tetrahedron Lett. 1972, 3451.
39. (b) Günther, H.; Peters, W.; Wehner, R. Chem. Ber. 1973, 106, 3683.
40. (c) Klärner, F.- G.; Tetrahedron Lett. 1974, 19.
41. (d) Stohrer, W.-D.; Daub, J. Angew. Chem. 1974, 86, 54.
42. (e) Wehner, R.; Günther, H. J. Am. Chem. Soc. 1975, 97, 923.
43. (f) Staley, S. W.; Fox, M. A.; Cairncross, A. Ibid, 1977, 99, 4524.
44. (g) Balci, M.; Fischer, H.; Günther, H. Angew. Chem. 1980, 92, 316.
45. (h) Takeuchi, K.; Arima, M.; Okamoto, K. Tetrahedron Lett. 1981, 22, 3081.
46. (i) Takeuchi, K.; Fujimoto, H.; Okamoto, K. Ibid. 1981, 22, 4981.
47. (j) Takeuchi, K.; Kitagawa, T.; Toyama, T.; Okamoto, K. J. Chem. Soc., Chem. Commun. 1982, 313.
48. (k) Takeuchi, K.; Kitagawa, T.; Senzaki, Y.; Fulimoto, H.; Okamoto, K. Chem. Lett. 1983, 69.
49. (l) Takeuchi, K.; Kitagawa, T.; Senzaki, Y.; Okamoto, K. Ibid. 1983, 73.
50. (m) Takeuchi, K.; Senzaki, Y.; Okamoto, K. J. Chem. Soc., Chem. Commun. 1984, 111.
51. (n) Takeuchi, K.; Fujimoto, H.; Kitagawa, T.; Fujii, H.; Okamoto, K. J. Chem. Soc., Perkin Trans. 2 1984, 461.
52. (o) Takeuchi, K.; Kitagawa, T.; Ueda, A.; Senzaki, Y.; Okamo, K. Tetrahedron 1985, 41, 5455.
53. Ingold, C. K. Structure and Mechanism in Organic Chemistry; Cornell University Press: Ithaca, NY, 1969; p 882.
54. (a) Hoffmann, R. Tetrahedron Lett. 1970, 2907.
55. (b) Günther, H. Ibid. 1970, 5173.
56. (a) Saba, A. Tetrahedron Lett. 1990, 32, 4657.
57. (b) Kohmoto, S.; Funabashi, T.; Nakayama, N.; Nishio, T.; Iida, I.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Org. Chem. 1993, 58, 4764.
58. (c) Oda, M.; Horiguchi, H.; Nasaki, Y.; Sakamoto, Y.; Kuroda, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 149.
59. (a) Matsumoto, M.; Shiono, T.; Mutoh, H.; Amano, M.; Arimitsu, S. J. Chem. Soc., Chem. Commun. 1995, 101.
60. (b) Matsumoto, M.; Shiono, T.; Kasuga, N. C. Tetrahedron Lett. 1995, 36, 8817.
61. (a) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543.
62. (b) Jeener, G.; Papadopoulos, M. J. Org. Chem. 1986, 51, 1, 585.
63. (c) Kohmoto, S.; Nakayama, N.; Takami, J.-i.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761.
64. (d) Oda, M.; Horiguchi, H.; Kajioka, T.; Kuroda, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 151.
65. (e) Kitagawa, T.; Miyabo, A.; Fujii, H.; Okazaki, T.; Mori, T.; Matsudou, M.; Sugie, T.; Takeuchi, K. J. Org. Chem. 1997, 62, 888.
66. (a) Roth, W. R.; Klärner, F. G.; Siepert, G.; Lennartz, H.-W. Chem. Ber. 1992, 125, 217.
67. (b) Dorn, H. C.; Yannoni, C. S.; Limbach, H.-H.; Vogel, E. J. Phys. Chem. 1994, 98, 11628.
68. (c) Laue, J.; Seitz, G. Liebigs Ann. Chem. 1996, 773.
69. (d) Mealli, C.; Ienco, A.; Hoyt, E. B.; Zoellner, R. W. Chem. Eur. J. 1997, 3, 958.
70. (a) Warner, P. M. J. Am. Chem. Soc. 1994, 116, 11059.
71. (b) Li, Z.; Shevlin, P. B. Ibid. 1997, 119, 1149.
72. (a) Gurskii, M. E.; Gridnev, I. D.; Geiderikh, A. V.; Ignatenko, A. V.; Bubnov, Y. N.; Mstislavky, V. I.; Ustynyuk, Y. A. Organometallics 1992, 11, 4056.
73. (b) Gurskii, M. E.; Gridnev, I. D.; Il'ichev, Y. V.; Ignatenko, A. V.; Bubnov, Y. N. Angew. Chem. 1992, 104, 762.
74. (c) Gridnev, I. D.; Gurskii, M. E.; Ignatenko, A. V.; Bubnov, Y. N.; Il'ichev, Y. V. Organometallics 1993, 12, 2487.
75. (d) Gurskii, M. E.; Gridnev, I. D.; Buevich, A. V.; Bubnov, Y. N. Organometallics 1994, 13, 4658.
76. (e) Gridnev, I. D.; Gurskii, M. E.; Buevich, A. V.; Bubnov, Y. N. Russ. Chem. Bull. 1996, 107.
77. (f) Gridnev, I. D.; Gurskii, M. E.; Bubnov, Y. N. Organometallics 1996, 15, 3696.
78. Kuwajima, S.; Soos, Z. G. J. Am. Chem. Soc. 1987, 109, 107.
79. (a) Staley, S. W.; Orvedal, A. W. J. Am. Chem. Soc. 1974, 96, 1618.
80. (b) Cunion, R. F.; Karney, W.; Wenthold, P. G.; Borden, W. T.; Lineberger, W. C. Ibid. 1996, 118, 5074.
81. (a) Moedritzer, K. Organomet. Chem. Rev. 1966, 1, 179.
82. (b) Hann, N. S.; Mole, T. Prog. NMR 1969, 4, 91.
83. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions; Clarendon: Oxford, 1987.
84. Perrin, C. L.; Dwyer, T. J. Chem. Rev. (Washington, D.C.) 1990, 90, 935.
85. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1990, 45, 1067.
86. Hehre, W. J. Acc. Chem. Res. 1975, 8, 369.
87. Kabakoff, D. S.; Namanworth, E. J. Am. Chem. Soc. 1970, 92, 3234.
88. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1984.
89. Friebolin, H. Ein- und zweidimensionale NMR-Spectroskopie, 2nd ed.; VCH: Weinheim, 1992.
90. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. (Washington, D.C.) 1988, 88, 899.
91. Pulay, P. In Modern Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum: New York, 1977; Vol. 4, p 153.
92. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
93. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
94. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
95. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head- Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
96. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
97. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
98. For a review of applications of DFT to electron-deficient rearrangements involving carbon see: Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F. In Modern Electronic Structure Theory and its Applications to Organic Chemistry; Davidson, E. L., Ed.; World Scientific Press: River Edge, NJ, in press.
99. (a) Spitznagel, G. W.; Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1982, 3, 363.
100. (b) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
101. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.