The reaction of [60]fullerene with lithium fluorenide: Formation of a novel 1,4-adduct of [60]fullerene

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7061-7064

  Murata, Yasujiro ^a   Komatsu, Koichi ^a   Wan, Terence S M ^b  

^a KYOTO UNIVERSITY   (Japan)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030599222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01552-3     Document Type: Article

References (25)

1. 1. For example, (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693.
2. b) Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994.
3. (c) Hirsch, A. Synthesis 1995, 895-913.
4. (d) An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein.
5. (e) Diederich, F.; Thilgen, C. Science 1996, 277, 317-323.
6. 2. Wudl, F.; Hirsh, A.; Khemani, K. C.; Suzuki, T.; Allemand, P. -M.; Koch, A.; Eckert, H.; Srdanov, G.; Webb, H. M. In Fullerenes Synthesis. Properties, and Chemistry of Large Carbon Clusters; Hammond, G. S., Kuck, V. J., Eds.; ACS Symposium Series 48, American Chemical Society: Washington, DC, 1992, pp 161-175.
7. 3. (a) Hirsch, A.; Soi, A.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 766-768.
8. (b) Hirsch, A.; Grosser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061-1067.
9. 4. Fagan, P. J.; Krusic, P. J.; Evans, D, H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699.
10. 5. The solvent-dependent formation of 1,4-bisadduct of silyhnethyl groups has been reported by Nagashima and coworkers: Nagashima, H.; Terasaki, H.; Kimura, E.; Nakajima, K.; Itoh, K. J. Org. Chem. 1994, 59, 1246-1248.
11. 6. (a) Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102.
12. (b) Murata, Y.; Motoyama, K.; Komatsu, K.; Wan, T. S. M. Tetrahedron 1996, 52, 5077-5090.
13. 7. (a) Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368.
14. (b) Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947.
15. 8. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
16. 9. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491.
17. 10: C, 98.86; H, 1.14. Found: C, 98.62; H, 1.23.
18. w = 0.052, GOF = 1.82, 1993 reflections with 1 > 3.0o(1). Further details are deposited with the Cambridge Crystallographic Data Centre.
19. 12. For example of a 1,2-bisadduct, see Ref. 8. For example of a Diels-Alder adduct, see Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344-345.
20. 18: C, 98.27; H, 1.73. Found: C, 98.11; H, 1.72.
21. 14. This is supposed to be due to hindered rotation of the fluorenyl groups. The results of preliminary studies on variable-temperature NMR indicate that the energy barrier for this rotation is nearly 12 kcal/mol. Results of the more detailed studies will be reported elsewhere.
22. 15. Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024.
23. 16. For the numbering system, see Taylor, R. J. Chem. Soc., Perkin. Trans. 2 1993, 813-824.
24. 22: C, 97.97; H, 2.03. Found: C, 97.64; H, 2.04.
25. 60 radical, see Ref. 4.