Novel methodology for the preparation of five-, seven-, and nine-membered fused rings on C60

Organic Letters

Volumn 8, Issue 9, 2006, Pages 1775-1778

  Hatzimarinaki, Maria ^a   Orfanopoulos, Michael ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646454882     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0600887     Document Type: Article

References (37)

1. For reviews on fullerene functionalization, see: (a) Wudl, F. In Buckminsterfullerenes; Billups, W. E., Ciufolini, M. A., Eds.; VCH Publishers: New York, 1993; Chapter 13.
2. (b) The Chemistry of Fullerenes; Taylor, R., Ed.; World, Scientific: Singapore, 1995.
3. (c) Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243.
4. (d) Prato, M.; Maggini, M. Acc. Chem. Res. 1998, 31, 519.
5. (e) Hirsch, A.; Brettreich, M. Fullerenes; Wiley-VCH Verlag Gmbh & Co. KGaA: 2005.
6. (f) Komatsu, K.; Murata, M.; Murata, Y. Science 2005, 307, 238.
7. (a) Akasaka, T.; Ando, W. J. Am. Chem. Soc. 1993, 115, 10366.
8. (b) Liou, K.-F.; Cheng, C.-H. Chem. Commun. 1996, 1423.
9. (c) Lawson, G. E.; Kitaygorodskiy, A.; Sun, Y.-P. J. Org. Chem. 1996, 61, 5913.
10. (d) Akasaka, T.; Maeda, Y.; Wakahara, T.; Okamura, M.; Fujitsuka, M.; Ito, O.; Kobayashi, K.; Nagase, S.; Kako, M.; Nakadaira, Y.; Horn, E. Org. Lett. 1999, 1, 1509.
11. (e) Mokami, K.; Matsumoto, S.; Okubo, Y.; Fujitsuka, M.; Ito, O.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 2236.
12. (f) Akasaka, T.; Maeda, Y.; Wakahara, T.; Mizushima, T.; Ando, W.; Wälchli, M.; Suzuki, T.; Kobayashi, K.; Nagase, S.; Kako, M.; Nakadaira, Y.; Fujitsuka, M.; Ito, O.; Sasaki, Y.; Yamamoto, K.; Erata, T. Org. Lett. 2000, 2, 2671.
13. (g) Imahori, H.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165.
14. (a) Arbogast, J. W.; Darmanyan, A. O.; Foote, C. S.; Rubin, Y.; Diederich, F. N.; Alvarez, M. M.; Anz, S. J.; Whetten, R. L. J. Phys. Chem. 1991, 95, 11.
15. (b) Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277.
16. (a) Vassilikogiannakis, G.; Orfanopoulos, M. Tetrahedron Lett. 1997, 24, 4323.
17. (b) Vassilikogiannakis, G.; Orfanopoulos, M. J. Am. Chem. Soc. 1997, 119, 7394.
18. (c) Vassilikogiannakis, G.; Hatzimarinaki, M.; Orfanopoulos, M. J. Org. Chem. 2000, 65, 8180.
19. (d) Vassilikogiannakis, G.; Chronakis, N.; Orfanopoulos, M. J. Am. Chem. Soc. 1998, 120, 9911.
20. For preparation of 1 and 7, see Supporting Information.
21. (a) Shimizu, N.; Nishida, S. J. Chem. Soc., Chem. Commun. 1972, 389.
22. (b) Rudolph, A.; Weedon, A. Can. J. Chem. 1990, 68, 1590.
23. (c) Becker, D.; Galili, N.; Haddad, N. Tetrahedron Lett. 1996, 37, 8941.
24. (d) Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A.; Weinkötz, S.; Winde, R. Chem.-Eur. J. 1997, 3, 105.
25. (a) Pasto, D. J. Tetrahedron Lett. 1973, 713.
26. (b) Sarel, S.; Felzenstein, A.; Yovell, J. Tetrahedron Lett. 1976, 451.
27. (c) Shimizu, N.; Fujioka, T.; Ishizuka, S.; Tsuji, T.; Nishida, S. J. Am.-Chem. Soc. 1977, 99, 5972.
28. (a) Kataoka, F.; Nishida, S. Chem. Lett. 1980, 1115-18.
29. (β) Tsuji, T.; Nishida, S. Acc. Chem. Res. 1984, 17, 56.
30. (b) Nishida, S.; Murakami, M.; Mizuno, T.; Tsuji, T.; Oda, H.; Shimizu, N. J. Org. Chem. 1984, 49, 3928.
31. Constantino, M. G.; da Silva, G. V. Tetrahedron 1998, 54, 11363.
32. Hatzimarinaki, M.; Roubelakis, M. M.; Orfanopoulos, M. J. Am. Chem. Soc. 2005, 127, 14183.
33. Cyclopropanes 5 and 6 were prepared according to the literature: Petersen, R. J.; Skell, P. S. Org. Synth. Coll. 1973, 5, 929.
34. Introduction to NMR spectroscopy; Abraham, R. J., Fisher, J., Loftus, P., Eds.; John Wiley and Sons Ltd.: New York, 1998.
35. (a) Walling, C.; Thaler, W. J. Am. Chem. Soc. 1961, 83, 3877.
36. (b) Krusic, P. J.; Meakin, P.; Smart, B. E. J. Am. Chem. Soc. 1974, 96, 6211.
37. (c) Korth, H.-G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483.