Thermal and Microwave-Assisted Synthesis of Diels-Alder Adducts of [60]Fullerene with 2,3-Pyrazinoquinodimethanes: Characterization and Electrochemical Properties

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3705-3710

  Fernández Paniagua, Ursula M ^a   Illescas, Beatriz ^a   Martín, Nazario ^a   Seoane, Carlos ^a   De la Cruz, Pilar ^b   De la Hoz, Antonio ^b   Langa, Fernando ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042969882     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701344     Document Type: Article

References (49)

1. (a) Hirsch, A. The Chemistry of the Fullerenes; Thieme Verlag: Stuttgart, 1994.
2. (b) Diederich, F.; Thilgen, C. Science 1996, 277, 317.
3. (c) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
4. (d) The Chemistry of Fullerenes; Taylor, R., Ed.; University of Sussex: World Scientific, 1995.
5. Hirsch, A. Synthesis 1995, 895.
6. For a review on o-quinodimethanes, see: Martin N.; Seoane, C.; Hanack M. Org. Prep. Proced. Int. 1991, 23, 237.
7. (a) Kraus, A.; Gügel, A.; Belik, P.; Walter, M.; Müllen, K. Tetrahedron 1995, 51, 9927.
8. (b) Belik, P.; Gügel, A.; Kraus, A.; Walter, M.; Müllen, K. J. Org. Chem. 1995, 60, 3307,
9. (c) Imahori, H.; Hagiwara, K.; Akiyama T.; Taniguchi, S.; Okada, T.; Sakata, Y. Chem. Lett. 1995, 265.
10. (d) Gügel, A.; Kraus, A.; Spickermann, J.; Belik, P.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 559.
11. (e) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929.
12. (f) Bidell, W.; Douthwaite, R. E.; Green, M. L. H.; Stephens, A. H.; Turner, J. F. C. J. Chem. Soc., Chem. Commun. 1994, 1641.
13. (g) Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235.
14. (h) Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
15. (i) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. See also: Meier, M. S. Chapter 10 in ref 1d.
16. (i) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. See also: Meier, M. S. Chapter 10 in ref 1d.
17. For a recent review on the synthesis of heterocycle-containing [60]fullerenes, see: Eguchi, S.; Ohno, M.; Kojima, S.; Koide, N.; Yashiro, A.; Shirakawa, Y.; Ishida, H. Fullerene Sci. Technol. 1996, 4, 303.
18. (a) Ando, K.; Takayama, H. Heterocycles 1994, 37, 1417.
19. (b) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. Chou, T.-S.; Chang, R.-C. J. Org. Chem. 1993, 58, 493.
20. (b) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. Chou, T.-S.; Chang, R.-C. J. Org. Chem. 1993, 58, 493.
21. (c) Chaloner, M. L.; Crew, A. P. A.; O'Neill, P. M.; Storr, R. C.; Yelland, M. Tetrahedron 1992, 48, 8101.
22. Fernández-Paniagua, U. M.; Illescas, B. M.; Martin, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077.
23. Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125.
24. Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials; Kadish, K. M., Ruoff, R. S., Eds.; The Electrochemical Society, Inc.: New Jersey, 1996; Vol. 3, pp 1233-1243.
25. (a) Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
26. (b) Abramovich, R. A. Org. Prep. Proced. Int. 1991, 23, 685.
27. (c) Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233.
28. (d) Caddick, S. Tetrahedron 1995, 51, 10403.
29. (e) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665.
30. (a) Motorina, I. A.; Parly, F.; Grieson, D. S. Synlett. 1996, 389.
31. (b) Huber, R. S.; Jones, G. B. J. Org. Chem. 1992, 57, 5778.
32. (c) Díaz-Ortiz, A.; Carrillo, J. R.; Díez-Barra, E.; de la Hoz, A.; Gómez-Escalonilla, M. J.; Moreno, A.; Langa, F. Tetrahedron 1996, 52, 9237.
33. Illescas, B.; Martín, N.; Seoane, C.; de la Cruz, P.; Langa, F.; Wudl, F. Tetrahedron Lett. 1995, 36, 8307.
34. de la Cruz, P.; de la Hoz, A.; Langa, F.; Illescas, B.; Martín, N. Tetrahedron 1997, 53, 2599.
35. Bandy, R. B.; Greenblatt, L. P.; Jirlobvsky, I. L.; Conklin, M.; Russo, R. J.; Bramlett, D. R.; Emrey, T. A.; Simmonds, J. T.; Kowal, D. M.; Stein, R. P.; Tasse, R. P. J. Med. Chem. 1993, 36, 331.
36. Alexandron, N. E.; Mertzanos, G. E.; Stephanidon-Stephanaton, J.; Tsoleridis, C. A.; Zaxharion, P. Tetrahedron Lett. 1995, 36, 6777.
37. For other recent precursors for quinoxalino-2,3-quinodimethanes, see: Chung, W.-S.; Liu, J.-H. Chem. Commun. 1997, 205.
38. Mattay, J. Communication presented to Fullerenes'96. Oxford, UK, July 1996.
39. Torres-García, G.; Mattay, J. Tetrahedron 1996, 52, 5421.
40. In the early experiments, domestic microwave ovens were used; this hardware had several limitations for using in laboratory. Home-made modifications were first performed, and specific designed apparatus have appeared later.
41. (a) Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc.1993, 115, 344.
42. (b) Tago, T.; Minowa, T.; Okada, Y.; Nishimura, J. Tetrahedron Lett. 1993, 34, 8461.
43. (c) Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235.
44. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London 1982; p 96.
45. (a) Ganapathi, P. S.; Friedman, S. H.; Kenyon, G. L.; Rubin, Y. J. Org. Chem. 1995, 60, 2954.
46. (b) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1995, 36, 6899.
47. Suzuki, T.; Maroyama, Y.; Akasaba, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359. See also: Eiermann, M.; Haddon, R. C.; Knight, B.; Li, Q.; Maggini, M.; Martín, N.; Ohno, T.; Prato, M.; Suzuki, T.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1591. Ohno, T.; Martin, N.; Knight, B.; Wudl, F.; Suzuki, T.; Yu, H. J. Org. Chem. 1996, 61, 1306.
48. Suzuki, T.; Maroyama, Y.; Akasaba, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359. See also: Eiermann, M.; Haddon, R. C.; Knight, B.; Li, Q.; Maggini, M.; Martín, N.; Ohno, T.; Prato, M.; Suzuki, T.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1591. Ohno, T.; Martin, N.; Knight, B.; Wudl, F.; Suzuki, T.; Yu, H. J. Org. Chem. 1996, 61, 1306.
49. Suzuki, T.; Maroyama, Y.; Akasaba, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359. See also: Eiermann, M.; Haddon, R. C.; Knight, B.; Li, Q.; Maggini, M.; Martín, N.; Ohno, T.; Prato, M.; Suzuki, T.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1591. Ohno, T.; Martin, N.; Knight, B.; Wudl, F.; Suzuki, T.; Yu, H. J. Org. Chem. 1996, 61, 1306.