Preparation of fullerendione through oxidation of vicinal fullerendiol and intramolecular coupling of the dione to form hemiketal/ketal moieties

Organic Letters

Volumn 8, Issue 2, 2006, Pages 277-279

  Huang, Shaohua ^a   Wang, Fudong ^a   Gan, Liangbing ^a,b   Yuan, Gu ^a   Zhou, Jiang ^a   Zhang, Shiwei ^c  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c Peking University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544440674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052602z     Document Type: Article

References (32)

1. (a) Rubin, Y. Top. Curr. Chem. 1999, 199, 67.
2. (b) Nierengarten, J.-F. Angew. Chem., Int. Ed. 2001, 40, 2973, and references therein.
3. (a) Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
4. (b) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
5. (a) Hummelen, J. C.; Bellavia-Lund, C.; Wudl, F. Top. Curr. Chem. 1999, 199, 93
6. (b) Prato, M.; Chan, L. Q.; Wudl, F.; Lucchini, V. J. Am. Chem. Soc. 1993, 115, 1148
7. (c) Shiu, L. L.; Chien, K. M.; Liu, T. Y.; Lin, T. I.; Her, G. R.; Luh, T. Y. J. Chem. Soc., Chem. Commun. 1995, 1159.
8. (a) Arce, M.-J.; Viado, A. L.; An, Y.-Z.; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 1996, 118, 3775.
9. (b) Qian, W.; Bartberger, M. D.; Pastor, S. J.; Houk, K. N.; Wilkins, C. L.; Rubin, Y. J. Am. Chem. Soc. 2000, 122, 8333.
10. (a) Hsiao, T.-Y.; Santhosh, K. C.; Liou, K.-F.; Cheng, C.-H. J. Am. Chem. Soc. 1998, 120, 12232.
11. (b) Murata, Y.; Kato, N.; Komatsu, K. J. Org. Chem. 2001, 66, 7235.
12. (c) Iwamatsu, S.; Vijayalakshmi, P. S.; Hamajima, M.; Suresh, C. H.; Koga, N.; Suzuki, T.; Murata, S. Org. Lett. 2002, 4, 1217.
13. (a) Schick, G.; Jarrosson, T.; Rubin, Y. Angew. Chem., Int. Ed. 1999, 38, 2360.
14. (b) Murata, Y.; Komatsu, K. Chem. Lett. 2001, 896.
15. (c) Y. Murata, M. Murata, K. Komatsu, J. Org. Chem. 2001, 66, 8187.
16. Hummelen, J. C.; Prato, M.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 7003.
17. (a) Komatsu, K.; Murata, M.; Murata, Y. Science 2005, 307, 238.
18. (b) Murata, Y.; Murata, M.; Komatsu, K. Chem. Eur. J. 2003, 9, 1600.
19. (c) Murata, Y.; Murata, M.; Komatsu, K. J. Am. Chem. Soc. 2003, 125, 7152.
20. (a) Gan, L. B.; Huang, S. H.; Zhang, X.; Zhang, A. X.; Cheng, B. C.; Cheng, H.; Li, X. L.; Shang, G. J. Am. Chem. Soc. 2002, 124, 13384.
21. (b) Xiao, Z.; Wang, F. D.; Huang, S. H.; Gan, L. B.; Zhou, J.; Yuan, G.; Lu, M. J.; Pan, J. Q. J. Org. Chem. 2005, 70, 2060.
22. (a) Huang, S. H.; Xiao, Z.; Wang, F. D.; Gan, L. B.; Zhang, X.; Hu, X. Q.; Zhang, S. W.; Lu, M. J.; Pan, J. Q.; Xu, L. J. Org. Chem. 2004, 69, 2442.
23. (b) Huang, S. H.; Xiao, Z.; Wang, F. D.; Zhou, J.; Yuan, G.; Zhang, S. W.; Chen, Z. F.; Thiel, W.; Schleyer, P. R.; Zhang, X.; Hu, X. Q.; Chen, B. C.; Gan, L. B. Chem. Eur. J. 2005, 11, 5449.
24. This is an improved method over the two step-reaction reported earlier in ref 10a.
25. For reviews, see: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
26. (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523;
27. For a recent example see: Kita, Y.; Matsuda, S.; Fujii, E.; Horai, M.; Hata, K.; Fujioka H. Angew. Chem., Int. Ed. 2005, 44, 5857.
28. (a) A. G. Avent, P. R. Birkett, H. W. Kroto, R. Taylor and R. M. Walton, J. Chem. Soc., Chem. Commun. 1998, 2153.
29. (b) Kitagawa, T.; Sakamoto, H.; Takeuchi, K. J. Am. Chem. Soc. 1999, 121, 4298.
30. (c) Murata, Y.; Cheng, F. Y.; Kitagawa, T.; Komatsu, K. J. Am. Chem. Soc. 2004, 126, 8874.
31. Lamparth, I.; Herzog, A.; Hirsch, A. Tetrahedron 1996, 52, 5065.
32. Karfunkel, H. R.; Dressler, T.; Hirsch, A. J. Comput.-Aided Mol. Design 1992, 6, 512.