Introduction of two benzyl groups to C60 by using the Collman reagent

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2049-2052

  Miki, Sadao ^a   Kitao, Masunori ^a   Fukunishi, Koushi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0029920649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00215-8     Document Type: Article

References (19)

1. Hirsch, A.; Soi, A.; Karfunkel, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 766-768. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S.; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102.
2. Hirsch, A.; Soi, A.; Karfunkel, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 766-768. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S.; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102.
3. Hirsch, A.; Soi, A.; Karfunkel, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 766-768. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S.; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102.
4. 60 with carbenes or ortho-quinodimethane are also attractive methods for the derivalization of the skeleton. (a) Wudl, F. Acc. Chem. Res. 1992, 25, 157-161 and references cited therein. Eiermann, M.; Wudl, F.; Prato, M.; Maggini, M. J. Am. Chem. Soc. 1994, 116, 8354-8365;
5. 60 with carbenes or ortho-quinodimethane are also attractive methods for the derivalization of the skeleton. (a) Wudl, F. Acc. Chem. Res. 1992, 25, 157-161 and references cited therein. Eiermann, M.; Wudl, F.; Prato, M.; Maggini, M. J. Am. Chem. Soc. 1994, 116, 8354-8365;
6. (b) Belik, P.; Gugel, A.; Spickmann, J.; Mullen, K. Angew. Chem. Int. Ed. Engl. 1993, 32, 78-80.
7. Nagashima, H.; Terasaki, H.; Kimura, E.; Nakajima, K.; Itoh, K. J. Org. Chem. 1994, 59, 1246-1248.
8. Kitagawa, T.; Tanaka, T.; Tanaka, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491.
9. Collman reagent was prepared according to the method reported in reference 9.
10. Hirsch, A.; Grosser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061-1067
11. (a) Mitsuzawa, N.; Dixon, D. A.; Fukunaga, T. J. Phys. Chem. 1992, 96, 7594-7604.
12. (b) Henderson. C. C.; Rohlfing, C. M.; Cahill, P. A. Chem Phys. Lett. 1993, 213, 383-388.
13. (c) Yoshida, Z.; Dogane, I.; Ikehira, H.; Endo, T. Chem Phys. Lett. 1993, 201, 481-484.
14. We appreciate discussions with Professor F. Wudl (UCSB) who suggested 1,4-adduct for our reaction product at the 3rd International Symposium on Functional Dyes (1995).
15. Colmann, J. P.; Finke, R. G.; Cawse, J. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 2515-2526.
16. 60 with iron carbonyl has been reported ; Douthwaite, R. E.; Green, M. L. H.; Stephens, A. H. H.; Turner, F. C. J. Chem. Soc. Chem. Comm., 1993, 1522-1523.
17. Collman, J. P. Acc. Chem. Res. 1975, 8, 342-347.
18. Cooke, Jr. M. P.; Parlman, R. M. J. Am. Chem. Soc. 1975, 97, 6863-6865.
19. Carton, C.; Subramanian, R.; D'Souza, F.; Kim, J.; Kutner, W.; Jones M. T.; Kadish, K. M.J. Am. Chem. Soc. 1993, 115, 8505-8506.