Benzyne adds across a closed 5-6 ring fusion in C70: Evidence for bond delocalization in fullerenes

Journal of the American Chemical Society

Volumn 120, Issue 10, 1998, Pages 2337-2342

  Meier, Mark S ^a   Wang, Guan Wu ^a   Haddon, Robert C ^a   Brock, Carolyn Pratt ^a   Lloyd, Michael A ^a   Selegue, John P ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BENZYNE; CARBON; FULLERENE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; CRYSTAL; CRYSTALLOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY;

EID: 0032542719     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973957j     Document Type: Article

References (64)

1. Haddon, R. C. Science 1993, 261, 1545-1550.
2. Hirsch, A. Synthesis 1995, 895-913.
3. Tetrahedron Symp. Print 60, 1996; Smith, A. B., III, Ed.
4. David, W. I. F.; Ibberson, R. M.; Matthewman, J. C.; Prassides, K.; Dennis, T. J. S.; Hare, J. P.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Nature 1991, 355, 147-149.
5. The Chemistry of Fullerenes; Taylor, R., Ed.; World Scientific: River Edge, NJ, 1995.
6. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699.
7. Balch, A. L.; Cullison, B.; Fawcett, W. R.; Ginwalla, A. S.; Olmstead, M. M.; Winkler, K. J. Chem. Soc., Chem. Commun. 1995, 2287-2288.
8. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
9. Kusukawa, T.; Ando, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1315-1317.
10. Wang, G.-W.; Shu, L.-H.; Wu, H.-M.; Lao, X.-F. J. Chem. Soc., Chem. Commun. 1995, 1071-1072.
11. Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024.
12. (a) Bergosh, R. G.; Meier, M. S.; Laske Cooke, J. A.; Spielmann, H. P.; Weedon, B. R. J. Org. Chem. 1997, 62, 7667-7672;
13. (b) For an extensive review of reduced fullerenes. see: Gol'dshleger, N. F.; Moravshii, A. P. Russ. Chem. Rev. 1997, 66, 323-342.
14. Meier, M. S. In ref 5, pp 174-194.
15. An earlier report of 5-6 closed adducts was found to be in error. For details, see: Schick, G.; Grösser, T.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2289-2290.
16. Godly, E. W.; Taylor, R. Pure Appl. Chem. 1997, 69, 1411-1434.
17. 70 adducts should display the same number of carbon resonances, and thereby casting doubt on some published structural assignments: Darwish, A. D.; Avent, A. G.; Taylor, R.; M., W. D. R. J. Chem. Soc., Perkin Trans. 2 1996, 2079-2084.
18. Darwish, A. D.; Abdul-Sada, A. K.; Langley, G. J.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1994, 2133-2134.
19. Meier, M. S.; Selegue, J. P. J. Org. Chem. 1992, 57, 1924-1926.
20. Wilson, S. R.; Lu, Q. J. Org. Chem. 1995, 60, 6496-6498.
21. Meier, M. S.; Poplawska, M.; Compton, A. L.; Shaw, J.; Selegue, J. P.; Guarr, T. F. J. Am. Chem. Soc. 1994, 116, 7044-7048.
22. Henderson, C. C.; Rohlfing, C. M.; Gillen, K. T.; Cahill, P. A. Science 1994, 264, 397-399.
23. Herrmann, A.; Diederich, F.; Thilgen, C.; ter Meer, H.-U.; Müller, W. H. Helv. Chim. Acta 1994, 77, 1689-1706.
24. Hawkins, J. M.; Meyer, A.; Solow, M. A. J. Am. Chem. Soc. 1993, 115, 7499-7500.
25. Avent, A. G.; Darwish, A. D.; Heimbach, D. K.; Kroto, H. W.; Meidine, M. F.; Parsons, J. P.; Remars, C.; Roers, R.; Ohashi, O.; Taylor, R.; Walton D. R. M. J. Chem. Soc., Perkin Trans. 2 1994, 15-22.
26. Balch, A. L.; Catalano, V. J.; Lee, J. W.; Olmstead, M. M.; Parkin, S. R. J. Am. Chem. Soc. 1991, 113, 8953-8955.
27. Balch, A. L.; Lee, J. W.; Olmstead, M. M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1356-1358.
28. Bellavia-Lund, C.; Wudl, F. J. Am. Chem. Soc. 1997, 119, 943-946.
29. Gerst, M.; Beckhaus, H.-D.; Rüchardt, C.; Campbell, E. E. B.; Tellgmann, R. Tetrahedron Lett. 1993, 34, 7729-7732.
30. Seiler, P.; Herrmann, A.; Diederich, F. Helv. Chim. Acta 1995, 78, 344-354.
31. Wilson, S. R.; Wu, Y. J. Am. Chem. Soc. 1993, 115, 10334-7.
32. Wood, J. M.; Kahr, B.; Hoke, S. H. I.; Dejarme, L.; Cooks, R. G.; Ben-Amotz, D. J. Am. Chem. Soc. 1991, 113, 5907-5908.
33. Smith, A. B. I.; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt, R. J.; King, R. C. J. Am. Chem. Soc. 1995, 117, 5492-5502.
34. Wang, Y.; Schuster, D. I.; Wilson, S. R.; Welch, C. J. J. Org. Chem. 1996, 67, 5198-5199.
35. Zhang, X.; Fan, A.; Foote, C. S. J. Org. Chem. 1996, 61, 5456-5461.
36. Bingel, C. Chem. Ber. 1993, 126, 1957-1959.
37. Bürgi, H. B.; Venugopalan, P.; Schwarzenbach, D.; Diederich, F.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2155-2159.
38. Kaupp, G.; Boy, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 48-49.
39. Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. Acta Crystallogr., Sect. C 1996, 52, 177.
40. Toda, F.; Tanaka, K.; Sano, I.; Isozaki, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1757.
41. Allen, F. H.; Kennard, O.; Taylor, R. Acc. Chem. Res. 1983, 16, 146-153.
42. Ishida, T.; Shinozuka, K.; Nogami, T.; Sasaki, S.; Iyoda, M. Chem. Lett. 1995, 317-318.
43. Osterodt, J.; Nieger, M.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1994, 1607-1608.
44. Anderson, H. L.; Boudon, C.; Diederich, F.; Gisselbrecht, J.-P.; Gross, M.; Seiler, P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1628-1632.
45. Paulus, E. F.; Bingel, C. Acta Crystallogr., Sect. C 1995, 51, 143.
46. Lamparth, I.; Maichle-Mossmer, C.; Hirsch, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1607-1609.
47. Tezuka, Y.; Kawasaki, N.; Yajima, H.; Ishii, T.; Oyama, T.; Takeuchi, K.; Katayama, C. Acta Crystallogr., Sect. C 1996, 52, 1008.
48. Balch, A. L.; Ginwalla, A. S.; Olmstead, M. M.; Herbst-Immer, R. Tetrahedron 1996, 553, 5021-5032.
49. Diederich, F.; Jonas, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thigen, C. Helv. Chem. Acta 1993, 76, 2445.
50. Belik, P.; Gugel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Mullen, K. Adv. Mater. 1993, 5, 854.
51. Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344-345.
52. Kräutler, B.; Muller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204.
53. Ramm, M.; Luger, P.; Averdung, J.; Mattay, J. Acta Crystallogr., Sect. C 1996, 52, 2590-2594.
54. Prato, M.; Wudl, F. In ref 5, pp 151-173.
55. Binsch, G.; Tamir, I. J. Am. Chem. Soc. 1969, 91, 2450-2455.
56. Haddon, R. C.; Brus, L. E.; Raghavachari, K. Chem. Phys. Lett. 1986, 125, 459-464.
57. Haddon, R. C.; Brus, L. E.; Raghavachari, K. Chem. Phys. Lett. 1986, 131, 165.
58. Haddon, R. C.; Schneemeyer, L. F.; Waszcak, J. V.; Glarum, S. H.; Tycko, R.; Dabbagh, G.; Kortan, A. R.; Muller, A. J.; Mujsce, A. M.; Rosseinsky, M. J.; Zahurak, S. M.; Makhija, A. V.; Thiel, F. A.; Raghavachari, K.; Cockayne, E.; Elser, V. Nature 1991, 350, 46-47.
59. Ruoff, R. S.; Beach, D.; Cuomo, J.; McGuire, T.; Whetten, R. L.; Diederich, F. J. Phys. Chem. 1991, 95, 3457-3459.
60. Saunders, M.; Jiménez-Vásquez, H. A.; Cross, R. J.; Mroczkowski, S.; Freedberg, D. I.; Anet, F. A. L. Nature 1994, 367, 256-258.
61. Saunders, M.; Jiménez-Vásquez, H. A.; Cross, R. J.; Billups, W. E.; Gesenberg, C.; Gonzales, A.; Luo, W.; Haddon, R. C.; Diederich, F.; Herrmann, A. J. Am. Chem. Soc. 1995, 117, 9305-9308.
62. Scuseria, G. E. Chem. Phys. Lett. 1991, 180, 451-456.
63. Sheldrick, G. M. SHELXL PC, Release 4.1; Siemens Analytical Instuments, Inc., 1990.
64. Sheldick, G. M. SHELXL 93. Program for the Refinement of Crystal Structures; University of Göttingen, 1993.