Synthesis and self-photooxygenation of alkenyl-linked [60]fullerene derivatives. A regioselective ene reaction

Organic Letters

Volumn 4, Issue 6, 2002, Pages 945-948

  Chronakis, Nikos ^a   Vougioukalakis, Georgios C ^a   Orfanopoulos, Michael ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041808822     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025690l     Document Type: Article

References (26)

1. Mattay, J.; Ulmer, L. Sotzmann, A. Photophysics and Photochemistry of Fullerenes and Fullerene Derivatives; Rumamurthy, V., Schanze, K. S., Eds. In Molecular and Supramolecular Photochemistry: Marcel Dekker: New York, 2001.
2. Hirsh, A. The Chemistry of the Fullerenes; Thieme Verlag: Stuttgart, 1994.
3. Arbogast, J. W.; Darmanyan, A. P.; Foote, C. S.; Rubin, Y.; Diederich, F. N.; Alvarez, M. M.; Anz, S. J.; Whetten, R. L. J. Phys. Chem. 1991, 95, 11.
4. (a) Orfanopoulos, M.; Kambourakis, S. Tetrahedron Lett. 1994, 35, 1945.
5. (b) Tokuyama, H.; Nakamura, E. J. Org. Chem. 1994, 59, 1135.
6. Zhang, X.; Romero, A.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 11024.
7. Ruoff, R. S.; Tse, D. S.; Malhotra, R.; Lorents, D. C. J. Phys. Chem. 1993, 97, 3379.
8. (a) An, Y.-Z.; C.-h. B.; Aderson, J. L.; Sigman, D. S.; Foote, C. S.; Rubin, Y. Tetrahedron 1996, 89, 5179.
9. (b) Boutorine, A. S.; Tokuyama, H.; Takasusi, M.; Isobe, H.; Nakamura, E.; Helene, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462.
10. An, Y.-Z.; Viado, A. L.; Arce, M.-J.; Rubin, Y. J. Org. Chem. 1995, 60, 8330.
11. Vassilikogiannakis, G.; Chronakis, N.; Orfanopoulos, M. J. Am. Chem. Soc. 1998, 120, 9911.
12. Caron, C.; Subramanian, R.; D'Souza, F.; Kim, J.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Am. Chem. Soc. 1993, 115, 8505.
13. (a) Subramanian, R.; Kadish, K. M.; Vijayashree, M. N.; Gao, X.; Jones, M. T.; Miller, M. D.; Krause, K. L.; Suenobu, T.; Fukuzumi, S. J. Phys. Chem. 1996, 100, 16327.
14. (b) Fukuzumi, S.; Suenobu, T.; Hirasaka, T.; Arakawa, R.; Kadish, K. M. J. Am. Chem. Soc. 1998, 120, 9220.
15. (a) Subramanian, R.; Boulas, P.; Vijayashree, M. N.; D'Souza, F.; Jones, M. T.; Radish, K. M. J. Chem. Soc., Chem. Commun. 1994, 1847.
16. (b) Allard, E.; Riviére, L.; Delaunay, J.; Dubois, D.; Cousseau, J. Tetrahedron Lett. 1999, 40, 7223.
17. Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; King, R. C. J. Am. Chem. Soc. 1993, 115, 5829.
18. For recent reviews on singlet oxygen, see: (a) Stratakis, M.; Orfanopoulos, M. Tetrahedron 2000 56, 1595.
19. (b) Clennan, E. L. Tetrahedron 2000, 56, 6945.
20. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697.
21. 2 afforded the desired allylic bromide in good yield.
22. cis-1-Bromo-2-butene was obtained from the key intermediate cis-methyl-2-butenoate: Orfanopoulos, M.; Smonou, I.; Foote, C. S. J. Am. Chem. Soc. 1990, 112, 3607.
23. Crawford, R. J.; Hamelin, J.; Strehlke, B. J. Am. Chem. Soc. 1971, 93, 3810.
24. Singlet oxygen ene reaction with cis-butene proceeds 20 times faster than that of the trans isomer: see ref 17.
25. (a) Foote, C. S. Acc. Chem. Res. 1968, 1, 104.
26. (b) Hurst, J. R.; Wilson, S. L.; Schuster, G. B. J. Am. Chem. Soc. 1982, 104, 2065.