Theoretical study of cycloaddition reactions of heavy carbenes with C 60

Journal of Physical Chemistry A

Volumn 111, Issue 28, 2007, Pages 6232-6240

  Lan, Chao Ying ^a   Su, Ming Der ^a  

^a NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CYCLOADDITION; POTENTIAL ENERGY SURFACES; THERMODYNAMICS;

CYCLOADDITION REACTIONS; HEAVY CARBENES; REACTION BARRIER HEIGHTS; VALENCE ELECTRONS;

OLEFINS;

EID: 34547514769     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp072400f     Document Type: Article

References (118)

1. Kroto, H. W.; Heath, J. R.; O'Brien, S. C; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 354.
2. (a) Kratschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
3. (b) Kratschmer, W.; Fostiropoulos, K.; Huffman, D. R. Chem. Phys. Lett. 1990, 170, 167.
4. For reviews, see: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
5. (b) Hirsch, A. Angew. Chem. 1993, 105, 1189.
6. For reviews, see: (a) Diederich, F.; Isaacs, L.; Philp, D. J. Chem. Soc. Rev. 1994, 243.
7. (b) Wrotnowski, C. Genet. Eng. News 1994, 36.
8. (c) Li, W. Z.; Qian, K. X.; Huang, W. D.; Zhang, X. X.; Chen, W. X. Chin. Phys. Lett. 1994, 11, 207.
9. (d) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Helene, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462.
10. (e) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem. 1996, 4 (6), 767.
11. For instance, see: (a) Benito, A. M.; Darwish, A. D.; Kroto, H. W.; Meidine, M. F.; Taylar, R.; Walton, D. R. M. Tetrahedron Lett. 1996, 37, 1085.
12. (b) Li, Z.;.Bouhadir, K. H.; Shevlin, P. B. Tetrahedron Lett. 1996, 37, 4651.
13. (c) Osterodt, J.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1996, 547.
14. (d) Kieluy, A. F.; Haddon, R. C; Meier, M. S.; Selegue, J. P.; Brock, C. P.; Patrick, B. O.; Wang, G.-W.; Chen, Y. J. Am. Chem. Soc. 1999, 121, 7971.
15. (e) Dong, G.-X.; Li, J.-S.; Chan, T.-K. J. Chem. Soc., Chem. Commun. 1995, 1725.
16. (f) Wand, N.; Li, J.; Zhu, D. T.; Chan, H. Tetraedron Lett. 1995, 36, 431.
17. (g) Schick, G.; Grösser, T.; Hirch, A. J. Chem. Soc., Chem. Commun. 1995, 2289.
18. (h) Averdung, J.; Wolff, C.; Mattay, J. Tetrahedron Lett. 1996, 37, 4633.
19. (i) Smith, A. B., III; Tokuyama, H. Tetrahedron 1996, 52, 5257.
20. (j) Tsuda, M.; Ishida, T.; Nogami, T.; Nogami, S.; Ohashi, M. Tetrahedron Lett. 1993, 34, 6911.
21. (k) Tokuyama, H.; Nakamura, M.; Nakamura, E. Tetrahedron Lett. 1993, 34, 7429.
22. (l) Bestmann, H. J.; Hadawi;D.; Roder, T.; Moll, C. Tetrahedron Lett. 1994, 35, 9017.
23. (m) Wan, Y.; Cao, J.; Shuster, D. I.; Wilson, R. R. Tetrahedron Lett. 1995, 36, 6843.
24. For azafullerenes see: (a) Prato, M.; Prato, Q. C.; Wudl, F.; Wudl, V. J. Am. Chem., Soc. 1993, 115, 1148.
25. (b) Bellavia-Lund, C.; Wudl, F. J. Am. Chem. Soc. 1997, 119, 943.
26. (c) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Rankin, D. W. H. J. Chem. Soc, Chem. Commun. 1994, 1365.
27. (d) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. T. A.: Taylor, A. T. J. Chem. Soc., Chem. Commun. 1995, 885.
28. (e) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Miller, J. T. A.; Parkinson, J. A.; Rankin, D. W. H.; Taylor, A. A. T. J. Chem. Soc., Chem. Commun. 1995, 887.
29. (f) Kuwashima, S.; Kubota, M.; Kushida, K.; Ishida, T.; Ohashi, M.; Nogami, T. Tetrahedron Lett. 1994, 35, 4371.
30. For methanofullerenes see: (a) Wudl, F. Acc. Chem. Res. 1992, 25, 157.
31. (b) Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 23, 243.
32. (c) Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F.; Almarsson, Ö. Science 1991, 254, 1186.
33. (d) Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. J. Am. Chem. Soc. 1992, 114, 7301.
34. (e) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; King, R. C. J. Am. Chem. Soc 1993, 115, 5829.
35. (f) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Owens, K. G.; Goldschmidt, J. Chem. Soc., Chem. Commun. 1994, 2187.
36. For oxafullerenes see: (a) Diedrich, F.; Eubin, R.; Whetten, R. L.; Beck, R.; Alvarez, M.; Anz, S.; Sensharma, D.; Wudl, F.; Khemani, K. C.; Koch, A. Science 1991, 252, 548.
37. (b) Creegan, K. M.; Robbins, J. L.; Robbins, W. K.; Millar, J. M.; Sherwood, R. D.; Tindall, P. J.; Cox, D. M.; Smith, A. B.; McCauley, J. P., Jr.; Jones, D. R.; Gallagher, T. T. J. Am. Chem. Soc. 1992, 114, 1103.
38. (c) Elemes, Y.; Silverman, S. K.; Sheu, C.; Cao, M. K.; Foote, C. S.; Alvarez, M. M.; Whetten, R. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 351.
39. (d) Julia, L.; Hamplova, V.; Kodymova, J.; Spalek, O. J. Chem. Soc., Chem. Commun. 1994, 2437.
40. (e) Hamano, T.; Mashino, T.; Hirobe, M. J. Chem. Soc., Chem. Commun. 1995, 1537.
41. For a review of silafullerenes see: (a) Ando, W.; Kusukawa, T. In The Chemistry of Organosilicon Compounds; Rapport, Z., Apeloig, Y., Eds.; John-Wiley & Sons: New York, 1929; Vol. 2, Chapter 1998, p 33. Silafullerenes:
42. (b) Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1993, 115, 1605.
43. (c) Akasaka, T.; Mitsuhida, E.; Ando, W.; Kobayashi, K.; Nagase, S. J. Chem. Soc., Chem. Commun. 1995, 1529.
44. (d) Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1993, 115, 10366.
45. (e) Akasaka, T.; Mitsuhida, E.; Mitsuhida, W.; Mitsuhida, K.; Nagase, S. J. Am Chem. Soc. 1994, 116, 2627.
46. (f) Akasaka, T.; Akasaka, Y.; Wakahara, T.; Mizushima, T.; Ando, W.; Wälchli, M.; Suzuki, T.; Suzuki, K.; Nagase, S.; Kako, M.; Nakadaira, Y.; Fujitsuka, M.; Ito, O.; Sasaki, Y.; Yamamoto, K.; Erata, T. Org. Lett. 2000, 2, 2671.
47. (g) Erata, T.; Kabe, Y.; Ando, W. Organometallics 1995, 14, 2142.
48. Prato, M.; Wudl, F. In The Chemistry of Fullerenes; Taylor, R., Ed.; World Scientific: New York; 1995, Vol. 4, pp 151-173.
49. Osterodt, J.; Vögtle, F. J. Chem. Soc. Chem. Commun. 1996, 547.
50. (a) Fagan, P. J.; Calabrese, J. C.; Malone, B. Science 1991, 252, 1160.
51. (b) Hawkins, J. M.; Meyer, A.; Lewis, T. A.; Loren, S.; Hollander, F. J. Science 1991, 252, 312.
52. (c) Balch, A. L.; Catalano, V. J.; Lee, J. W. Inorg. Chem. 1991, 30, 3980.
53. (d) Fagan, P. J.; Calabrese, J. C.; Malone, B. J. Am. Chem. Soc 1991, 113, 9408.
54. (e) Balch, A. L.; Catalano, V. J.; Lee, J. W.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 5455.
55. (f) Hawkins, J. M.; Meyer, A.; Lewis, T. A.; Loren, S.; Hollander, F. J. Science, 1991, 252, 312.
56. (g) Balch, A. L.; Lee, J. W.; Noll, B. C.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 10984.
57. (h) Bashilov, V. V.; Petrovskii, P. V.; Sokolov, V. I.; Lindeman, S. V.; Guzey, I. A.; Struchkov, Y. T. Organometallics 1993,12, 991.
58. (i) Balch, A. L.; Lee, J. W.; Noll, B. C.; Olmstead, M. M. Inorg. Chem. 1993, 32, 3577.
59. (j) Mavunkal, I. P.; Chi, Y.; Peng, S.-M.; Lee, G.-H. Organometallics 1995, 14, 4454.
60. (k) Lee, K.; Hsu, H,F.; Shapley, J. R. Organometallics 1997, 16, 3876.
61. (l) Sawamura, M.; Kuninonu, Y.; Nakamura. E. J. Am. Chem. Soc. 2000, 722, 12407.
62. (m) Park, J. T.; Song, H.; Lee, K.; Lee, C. H. Angew. Chem., Int. Ed. 2001, 40, 1500.
63. (n) Sawamura, M.; Kuninonu, Y.; Taganoh, M.; Matsuo, Y.; Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2002, 124, 9354.
64. (o) Matsuo, Y.; Mitani, Y.; Zhong, Y.-W.; Nakamura. E. Organometallics 2006, 25, 2826.
65. For instance, see: (a) Koga, N.; Morokuma, K. Chem. Phys. Lett. 1993, 202, 330.
66. (b) Rogers, J.; Marynick, D. S. Chem. Phys. Lett. 1993, 205, 197.
67. (c) Lichtenberger, D. L.; Wright, L. L.; Gruhn, N. E.; Rempe, M. E. Synth. Met. 1993, 59, 353.
68. (d) Fujimoto, H.; Nakao, Y.; Fukui, K. J. Mol. Struct. 1993, 300, 425.
69. (e) López, J. A.; Mealli, C. J. Organomet. Chem. 1994, 478, 161.
70. (f) Lichtenberger, D. L.; Wright, L. L.; Gruhn, N. E.; Rempe, M. E. J. Organomet. Chem. 1994, 478, 213.
71. (g) Bo, C.; Costas, M.; Poblet, J. M. J. Phys. Chem. 1995, 99, 5914.
72. (h) Nunzi, F.; Sgamellotti, A.; Re, N.; Floriáni, C. Organometallic 2000, 19, 1628.
73. (i) Song, L.-C.; Liu, J.-T.; Hu, Q.-M.; Weng, L.-H. Organometallics 2000, 19, 1643.
74. (j) Jemmis, E. D.; Manoharan, M.; Sharma, P. K. Organometallics 2000, 19, 1879.
75. (k) Song, L.-C.; Liu, J.-T.; Hu, Q.-M.; Wang, G.-F.; Zanello, P.; Fontani, M. Organometallics 2000, 19, 5342.
76. (l) Babcock, A. J.; Li, J.; Lee, K.; Shapley, J. R. Organometallics 2002, 21, 3940.
77. (m) Kameno, Y.; Ikeda, A.; Nakao, Y.; Sato, H.; Sakaki, S. J. Phys. Chem. A 2005, 709, 8055.
78. For instance, see: (a) Hawkins, J. M.; Lewis, T. A.; Loren, S. D.; Meyer, A.; Heath, J. R.; Shibato, Y.; Saykally, R. J. J. Org. Chem. 1990, 55, 6250.
79. (b) Koefod, R. S.; Hudgens, M. F.; Shapley, J. R. J. Am. Chem. Soc. 1991, 113, 8957.
80. (c) Schreiner, S.; Gallaher, T. N.; Parsons, H. K. Inorg. Chem. 1994, 33, 3021.
81. (d) Park, J. T.; Cho, J.-J.; Song, H. J. Chem. Soc., Chem. Commun. 1995, 15.
82. (e) Sawamura, M.; Iikura, H.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 12850.
83. (f) Sawamura, M.; Iikura, H.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1998, 720, 8285.
84. (g) Sawamura, M.; Iikura, H.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 8285.
85. (h) Park, J. T.; Song, H.; Cho, J.-J.; Chung, M.-K.; Lee, J.-H.; Suh, I.-H. Organometallics 1998, 77, 227.
86. (i) Sawamura, M.; Toganoh, M.; Kuninobu, Y.; Kato, S.; Nakamura, E. Chem. Lett. 2000, 29, 270.
87. (j) Sawamura, M.; likura, H.; Ohama, T.; Hackler, U. E.; Nakamura, E. J. Organomet. Chem. 2000, 599, 32.
88. (k) Nakamura, E.; Sawamura, M. Pure Appl. Chem. 2001, 73, 355.
89. (l) Sawamura, M.; Toganoh, M.; Kuninobu, Y.; Kato, S.; Nakamura, E. Chem. Lett. 2000, 270.
90. (m) Sawamura, M.; likura, H.; Ohama, T.; Hackler, U. E.; Nakamura, E. J. Organomet. Chem. 2000, 599, 32.
91. (n) Sawamura, M.; Toganoh, M.; Suzuki, K.; Hirai, A.; Iikura, H.; Nakamura, E. Org. Lett. 2000, 2, 1919.
92. For instance, see: Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, W. J. Am. Chem. Soc. 1993, 115, 1605.
93. For instance, see: Kabe, Y.; Ohgaki, H.; Yamagaki, T.; Nakanishi, H.; Ando, E. J. Organomet. Chem. 2001, 636, 82.
94. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
95. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
96. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
97. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; AlLaham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 03; Gaussian, Inc.: Pittsburgh PA, 2003.
98. Gimarc, B. M. In Molecular Structure and Bonding; Academic Press: New York, 1979.
99. (a) Pykkö, P.; Desclaux, J.-P. Acc. Chem. Res. 1979, 72, 276.
100. (b) Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
101. (c) Pykkö, P. Chem. Rev. 1988, 88, 563.
102. (d) Pykkö, P. Chem. Rev. 1997, 97, 597.
103. (a) Su, M.-D. J. Phys. Chem. A 2002, 106, 9563.
104. (b) Su, M.-D. Eur. J. Chem. 2004, 10, 5877.
105. (a) David, W. I. F.; Ibberson, R. M.; Matthewman, J. C.; Prassides, K.; Dennis, T. J. S.; Hare, H. W.; Taylor, R.; Walton, D. R. M. Nature 1991, 353, 147.
106. (b) Hedberg, K.; Hedberg, L.; Bethune, D. S.; Brown, C. A.; Dorn, H. C.; Johnson, R. D.; de Vries, M. Science 1991, 254, 410.
107. Grebenik, M.; Downs, A. J.; Green, M. L. H.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1979, 742.
108. Chetwynd-Talbot, J.; Grebnik, P.; Perutz, R. N. Inorg. Chem. 1982, 21, 3647.
109. For instance, see: (a) Reference 5i.
110. (b) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Rankin, D. W. H. Synth. Met. 1996, 77, 77.
111. (c) Clare, B. W.; Kepert, D. L. THEOCHEM 2001, 548, 61.
112. (a) Liu, S.; Lu, Y.; Kappas, M. M.; Ibers, J. A. Science 1991, 254, 410. (b) Reference 23a.
113. For details, see: (a) Shaik, S.; Schlegel, H. B.; Wolfe, S. In Theoretical Aspects of Physical Organic Chemistry; John Wiley & Sons Inc.: New York, 1992.
114. (b) Pross, A. In Theoretical and Physical principles of Organic Reactivity; John Wiley & Sons Inc.: New York, 1995.
115. (c) Shaik, S. Prog. Phys. Org. Chem. 1985, 15, 197.
116. (a) For the first paper that originated the CM model see: Shaik, S. J. Am. Chem. Soc. 1981, 103, 3692.
117. (b) For the most updated review of the CM model, one can see: Shaik, S.; Shurki, A. Angew. Chem., Int. Ed. 1999, 38, 586.
118. Sheu, J.-H.; Su, M.-D. Eur. J. Chem. In press.