Photoinduced electron transfer reactivity of aza[60]fullerene: Three discrete functionalization pathways with a single substrate

Journal of the American Chemical Society

Volumn 126, Issue 49, 2004, Pages 15956-15957

  Vougioukalakis, Georgios C ^a   Orfanopoulos, Michael ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 10344239450     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045495x     Document Type: Article

References (24)

1. Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. Science 1995, 269, 1554-1556.
2. Nuber, B.; Hirsch, A. Chem. Commun. 1996, 1421-1422.
3. For some representative examples, see: (a) Prassides, K.; Keshavarz, K. M.; Hummelen, J. C.; Andreoni, W.; Giannozzi, P.; Beer, E.; Bellavia, C.; Cristofolini, L.; Gonzalez, R.; Lappas, A.; Murata, Y.; Malecki, M.; Srdanov, V.; Wudl, F. Science 1996, 271, 1833-1835. (b) Brown, C. M.; Beer, E.; Bellavia, C.; Cristofolini, L.; Gonzalez, R.; Hanfland, M.; Hauserman, D.; Keshavarz, K. M.; Kordatos, K.; Prassides, K.; Wudl, F. J. Am. Chem. Soc. 1996, 118, 8715-8716.
4. For some representative examples, see: (a) Prassides, K.; Keshavarz, K. M.; Hummelen, J. C.; Andreoni, W.; Giannozzi, P.; Beer, E.; Bellavia, C.; Cristofolini, L.; Gonzalez, R.; Lappas, A.; Murata, Y.; Malecki, M.; Srdanov, V.; Wudl, F. Science 1996, 271, 1833-1835. (b) Brown, C. M.; Beer, E.; Bellavia, C.; Cristofolini, L.; Gonzalez, R.; Hanfland, M.; Hauserman, D.; Keshavarz, K. M.; Kordatos, K.; Prassides, K.; Wudl, F. J. Am. Chem. Soc. 1996, 118, 8715-8716.
5. Ren, A.; Fens, J.; Sun, X.; Li, W.; Tian, W.; Sun, C.; Zhens, X.; Zerner, M. C. Int. J. Quantum Chem. 2000, 78, 422-436.
6. For reviews on the synthesis and reactivity of azafullerenes, see: (a) Hummelen, J. C.; Beliavia-Lund, C.; Wudl, F. Top. Curr. Chem. 1999. 199, 1-65. (b) Hirsch, A.; Nuber, B. Acc. Chem. Res. 1999, 32, 795-804. (c) Reuther, U.; Hirsch, A. Carbon 2000, 1539-1549.
7. For reviews on the synthesis and reactivity of azafullerenes, see: (a) Hummelen, J. C.; Beliavia-Lund, C.; Wudl, F. Top. Curr. Chem. 1999. 199, 1-65. (b) Hirsch, A.; Nuber, B. Acc. Chem. Res. 1999, 32, 795-804. (c) Reuther, U.; Hirsch, A. Carbon 2000, 1539-1549.
8. For reviews on the synthesis and reactivity of azafullerenes, see: (a) Hummelen, J. C.; Beliavia-Lund, C.; Wudl, F. Top. Curr. Chem. 1999. 199, 1-65. (b) Hirsch, A.; Nuber, B. Acc. Chem. Res. 1999, 32, 795-804. (c) Reuther, U.; Hirsch, A. Carbon 2000, 1539-1549.
9. Keshavarz, K. M.; Gonzalez, R.; Hicks, R. G.; Srdanov, G.; Srdanov, V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C.; Pavlovich, J.; Wudl, F.; Holczer, K. Nature 1996, 383, 147-150.
10. Bellavia-Lund, C.; Gonzalez, R.; Hummelen, J. C.; Hicks, R. G.; Sastre, A.; Wudl, F. J. Am. Chem. Soc. 1997, 119, 2946-2947.
11. Vougioukalakis, G. C.; Orfanopoulos, M. Tetrahedron Lett. 2003, 44, 8649-8652.
12. Nuber, B.; Hirsch, A. Chem. Commun. 1998, 405-406.
13. Hauke, F.; Hirsch, A. Chem. Commun. 1999, 2199-2200.
14. Hauke, F.; Hirsch, A. Tetrahedron 2001, 57, 3697-3708.
15. Hauke, F.; Herranz, M. A.; Echegoyen, L.; Guldi, D.; Hirsch, A.; Atalick, S. Chem. Commun. 2004, 600-601.
16. Hauke, F.; Atalick, S.; Guldi, D. M.; Mack, J.; Scott, L. T.; Hirsch, A. Chem. Commun. 2004, 766-767.
17. Kim, K. C.; Hauke, F.; Hirsch, A.; Boyd, P. D. W.; Carter, E.; Armstrons, R. S.; Lay, P. A.; Reed, C. A. J. Am. Chem. Soc. 2003, 125, 4024-4025.
18. For reviews on the photochemical transformations of iminium salts, see: (a) Mariano, P. S. Ace. Chem. Res. 1983, 16, 130-137. (b) Mariano, P. S. Tetrahedron 1983, 39, 3845-3879.
19. For reviews on the photochemical transformations of iminium salts, see: (a) Mariano, P. S. Ace. Chem. Res. 1983, 16, 130-137. (b) Mariano, P. S. Tetrahedron 1983, 39, 3845-3879.
20. Borg, R. M.; Heuckeroth, R. O.; Lan, A. J. Y.; Quillen, S. L.; Mariano, P. S. J. Am. Chem. Soc. 1987, 709, 2728-2737.
21. For self-photo-oxygenations of aza[60]fullerene and [60]fullerene adducts, see: (a) Tagmatarchis, N.; Shinohara, H.; Pichler, T.; Krause, M.; Kuzmany, H. J. Chem. Soc., Perkin Trans. 2 2000, 2361-2362. (b) Chronakis, N.; Vougioukalakis, G. C.; Orfanopoulos, M. Org. Lett. 2002, 4, 945-948.
22. For self-photo-oxygenations of aza[60]fullerene and [60]fullerene adducts, see: (a) Tagmatarchis, N.; Shinohara, H.; Pichler, T.; Krause, M.; Kuzmany, H. J. Chem. Soc., Perkin Trans. 2 2000, 2361-2362. (b) Chronakis, N.; Vougioukalakis, G. C.; Orfanopoulos, M. Org. Lett. 2002, 4, 945-948.
23. Vougioukalakis, G. C.; Chronakis, N.; Orfanopoulos, M. Org. Lett. 2003, 5, 4603-4606.
24. Gusel'Nikov, L. E.; Nametkin, N. S. Chem. Rev. 1979, 79, 529-577.