Synthesis of heterocycle-linked [60] fullerene derivatives by heterocyclic o-quinodimethane Diels-Alder reaction and self-sensitized photooxygenation of the cycloadducts

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9075-9086

  Ohno, Masatomi ^a   Koide, Naoya ^a   Sato, Haruhiko ^a   Eguchi, Shoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030979771     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00600-5     Document Type: Article

References (69)

1. For example, a) Kroto, H.; Fischer, J. E.; Cox, D. E. The Fullerenes, Pergamon Press, Oxford, 1993.
2. b) Hirsch, A. The Chemistry of Fullerenes, Georg Thime Verlag, Stuttgart, 1994.
3. (c) Kadish, K. M.; Ruoff, R. S. Eds. Recent Advances in the Chemistry and Physics of Fullerenes and Relate Materials, The Electrochemical Society, Inc.: New Jersey, 1994; pp. 698-789.
4. d) Williams, R. M.; Zwier, J. M.; Verhoeven, J. W. J. Am. Chem. Soc. 1995, 117, 4093.
5. e) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
6. Haddon, R. C. Science 1993, 261, 1545.
7. Rosen, A.; Wästberg, J. Chem. Phys. 1989, 90, 2525.
8. Recent reviews: a) Averdung, J.; Torres-Garcia, G.; Luftmann, H.; Schlachter, I.; Mattay, J. Fullerene Sci. Tech. 1996, 4, 633.
9. b) Hirsch, A. Synthesis 1995, 895.
10. (c) Sliwa, W. Fullerene Sci. Tech. 1995, 3, 243.
11. d) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243.
12. 70 Fullerenes In The Fullerenes; Kroto, H. W.; Fischer, J. E.; Cox, D. E. Eds.; Pergamon Press: Oxford, 1993; pp. 65-73.
13. f) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
14. g) Eguchi, S.; Ohno, M. Kikan Furaren 1993, 1 (3), 99.
15. a) Prato, M.; Lucchini, V.; Maggini, M.; Stimpfl, E.; Scorrano, G.; Eiermann, M.; Suzuki, T.; Wudl, F. J. Am. Chem. Soc. 1993, 115, 8479.
16. b) Banks, M. R.; Cadgan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R.; Millar, J. R. A.; Parkinson, J. A. ; Rankin, D. W. H.; Taylor, A. T. J. Chem. Soc., Chem. Commun. 1995, 887.
17. a) Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M. J. Chem. Soc., Chem. Commun. 1993, 1296.
18. b) Guhr, K. I.; Greaves, M. D.; Rotello, V. M. J. Am. Chem. Soc. 1994, 116, 5997.
19. a) Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 1594.
20. b) Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344.
21. c) Belik, P.; Gugel, J.; Spickermann, K.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
22. d) Tago, T.; Minowa, T.; Okada, Y.; Nishimura, J. Tetrahedron Lett. 1993, 34, 8461.
23. e) Diederich, F.; Jonas, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H., Thilgen, C. Helv. Chim. Acta. 1993, 76, 2445.
24. f) Zhang, X.; Foote, C. S J. Org. Chem. 1994, 59, 5235.
25. g) Herrmann, A.; Diederich, F. Thilgen, C. Helv. Chim. Acta. 1994, 77, 1689.
26. h) Gugel, A.; Kraus, A.; Spickermann, J.; Belik, P.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 559.
27. i) Bidell, W.; Douthwaite, R. E.; Green, M. L. H.; Stephens, A. H. H.; Turner, J. F. C. J. Chem. Soc., Chem. Commun. 1994, 1641.
28. j) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929.
29. k) Iyoda, M.; Sultana, F.; Sasaki, S.; Butenschön, H. Tetrahedron Lett. 1995, 36, 579.
30. l) Belik, P.; Gügel, A.; Kraus, A.; Walter, M.; Müllen, K. J. Org. Chem. 1995, 60, 3307.
31. m) Tomioka, H.; lchihashi, M.; Yamamoto, K. Tetrahedron Lett. 1995, 36, 5371.
32. n) Tomioka, H.; Yamamoto, K. J. Chem. Soc., Chem. Commun. 1995, 1961.
33. o) Seiler, P.; Herrmann, A.; Diederich, F. Helv. Chim. Acta. 1995, 78, 344.
34. p) Illescas, B.; Martin, N.; Seoane, C.; Cruz, P.; Langa, F.; Wudl, F. Tetrahedron Lett. 1995, 36, 8307.
35. q) Imahori, H.; Hagiwara, K.; Akiyama, T.; Taniguchi, S.; Okada, T.; Sakata, Y. Chem. Lett. 1995, 265.
36. r) Iyoda, M.; Sasaki, S.; Sultana, F.; Yoshida, M.; Kuwatani, Y.; Nagase, S. Tetrahedron Lett. 1996, 37, 7987. For the hetero version of o-quinodimethane, see:
37. s) Ohno, M.; Azuma, T.; Eguchi, S. Chem. Lett. 1993, 1833.
38. t) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1995, 36, 6899.
39. a) Ohno, M.; Kojima, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565.
40. b) Ohno, M.; Yashiro, A.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1996, 291.
41. c) Ohno, M.; Yashiro, A.; Eguchi, S. Synlett 1996, 815.
42. d)Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211. See also refs. 7s and 7t.
43. a) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Int. 1991, 23, 239.
44. b) Chou, T. S. Rev. Heteroatom Chem. 1993, 8, 65.
45. Ohno, M.; Koide, N.; Eguchi, S. Heterocyclic Commun. 1995, 1, 125.
46. Fernandez-Paniagua, U. M.; Illescas, B. M.; Martin, N.; Seoane, C. J. Chem. Soc., Perkin Trans. I 1996, 1077.
47. a) Arbogast, J. W., Darmanyan, A. P.; Foote, C. S.; Rubin, Y.; Diederich, F.; Alvarez, M. M.; Anz, S. J.; Whetten, R. J. J. Phy. Chem. 1991, 95, 11.
48. b) Wasielewsky, M. R.; O'Neil, M. P.; Lykke, K. R.; Pellin, M. J.; Gruen, D. M. J. Am. Chem. Soc. 1991, 113, 2774.
49. Trahanovsky, W. S.; Cassady, T. J.; Woods, T. L. J. Am. Chem. Soc. 1981, 103, 6691.
50. Chadwick, D. J.; Plant, A. Tetrahedron Lett. 1987, 28, 6085.
51. Chou, T. S.; Chen, H. C.; Tsai, C. Y. J. Org. Chem. 1994, 59, 2241.
52. Chou, T. S.; Tsai, C. Y. Tetrahedron Lett. 1992, 33, 4201.
53. Saroja, B.; Srinivasan, P. C. Tetrahedron Lett. 1984, 25, 5429.
54. Wegmann, J.; Dahn, H. Helv. Chim. Acta. 1946, 29, 101.
55. Alexandrou, N. E.; Mertzanos, G. E.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A.; Zachariou, P. Tetrahedron Lett. 1995, 36, 6777.
56. Wilson, S. R.; Lu, Q. Tetrahedron Lett. 1993, 3-4, 8043.
57. Wasserman, H. W.; Lipshutz, B. H. Reactions of Singlet Oxygen with Heterocyclic Systems In Singlet Oxygen; Wasserman, H. W.; Murray, R. W. Eds.; Academic Press: New York, 1979; pp. 430-509.
58. Tokuyama, H.; Nakamura, E. J. Org. Chem. 1994, 59, 1135. See also: Anderson, J. L.; An, Y.-Z.; Rubin, Y.; Foote, C. S. J. Am. Chem. Soc. 1994, 116, 9763.
59. Tokuyama, H.; Nakamura, E. J. Org. Chem. 1994, 59, 1135. See also: Anderson, J. L.; An, Y.-Z.; Rubin, Y.; Foote, C. S. J. Am. Chem. Soc. 1994, 116, 9763.
60. a) An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353.
61. b) An, Y.-Z.; Viado, A. L.; Arce, M.-J.; Rubin, Y. J. Org. Chem. 1995, 60, 8330.
62. c) Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 4271.
63. d) Zhang, X.; Fan, A.; Foote, C. S. J. Org. Chem. 1996, 61, 5456.
64. e) Torres-Garcia, G.; Mattay, J. Tetrahedron 1996, 52, 5421. For the oxygenation of [5.6]azafulleroid ring itself, see: Hummelen, J. C.; Prato, M.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 7003.
65. e) Torres-Garcia, G.; Mattay, J. Tetrahedron 1996, 52, 5421. For the oxygenation of [5.6]azafulleroid ring itself, see: Hummelen, J. C.; Prato, M.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 7003.
66. Zhang, X.; Romero, A.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 11024.
67. Foote, C. S.; Wuesthoff, M. T.; Wexler, S.; Burstain, I. G.; Denny, R.; Schenck, G. O.; Schulte-Elte, K.-H. Tetrahedron 1967, 23, 2583.
68. Wasserman, H. H.; Druckrey, E. J. Am. Chem. Soc. 1968, 90, 2440.
69. The cycloaddition was attempted by using N-phenyl-4,5-dimethylene-2-oxazolidinone (Hernández, R.; Sánchez, J. M.; Gómez, A.; Trujillo, G.; Aboytes, R.; Zepeda, G.; Bates, R. W.; Tamariz, J. Heterocycles 1993, 36, 1951) as an example of nonaromatic heterocyclic exo-diene, but no cycloadduct was obtained, indicating limits to this approach.