One-step multiple addition of amine to [60]fullerene. Synthesis of tetra(amino)fullerene epoxide under photochemical aerobic conditions

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3663-3665

  Isobe, Hiroyuki ^a   Tomita, Naoki ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000060050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006573y     Document Type: Article

References (12)

1. (a) Sawamura, M.; Iikura, H.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 12850.
2. (b) Sawamura, M.; Iikura, H.; Ohama, T.; Hackler, U. E.; Nakamura, E. J. Organomet. Chem. 2000, 599, 32.
3. (c) Sawamura, M.; Toganoh, M.; Kuninobu, Y.; Kato, S.; Nakamura, E. Chem. Lett. 2000, 262.
4. (a) Krusic, P. J.; Wasserman, E.; Keizer, P. N.; Morton, J. R.; Preston, K. F. Science 1991, 254, 1183.
5. (b) Birkett, P. R.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.; Taylor, R., Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1993, 1230.
6. (c) Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023.
7. (d) Murata, Y.; Shiro, M.; Komatsu, K. J. Am. Chem. Soc. 1997, 119, 8117.
8. 3) δ 46.07, 46.09, 50.42. 50.78, 55.65. 55.76, 71.53, 71.83, 75.44, 76.31, 140.07, 141.48, 142.71, 142.90, 143.30, 143.41, 143.68, 143.87, 144.09 144.45, 144.93, 145.10, 145.96, 146.12, 146.65, 146.71, 146.76, 146.79, 146.81, 146.91, 147.22, 147.50, 147.58, 148.88, 149.11, 149.14, 149.17, 151.21.
9. When a small excess of 1-methylpiperazine was used, a demethylative monoadduct (see below) formed as a major side product (ca. 10%; Kampe, K.-D.; Egger, N. Liebigs Ann. 1995, 115), which does not form, however, when > 16 equiv of the amine was used for the reaction. Note that this monoadduct does not react further with 1-methylpiperazine, failing to give the multiple adduct 1. matrix presented
10. Sawamura, M.; Toganoh, M.; Suzuki, K.; Hirai, A.; Iikura, H.; Nakamura, E. Org. Lett. 2000, 2, 1919.
11. Isobe, H.; Ohbayashi, A.; Sawamura, M.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 2669.
12. Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem. In press.