A ready access to unprecedented N-anilinopyrazolino[60]fullerenes

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1651-1654

  Delgado, Juan L ^a   De La Cruz, Pilar ^a   López Arza, Vicente ^a   Langa, Fernando ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Amino; Pyrazoline 60 fullerene

Indexed keywords

FULLERENE DERIVATIVE; PYRAZOLINE DERIVATIVE;

ALKALINIZATION; ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; MATERIAL STATE; REDUCTION; SOLVENT EFFECT;

EID: 0842348307     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.111     Document Type: Article

References (22)

1. Hirsch A. Fullerenes and Related Structures. Vol. 199:1999;Springer, Berlin.
2. Diederich F., Thilgen C. Science. 271:1996;317-323.
3. Echegoyen L., Echegoyen L.E. Acc. Chem. Res. 31:1998;593-601.
4. Imahori H., Sakata Y. Adv. Mater. 9:1997;537-546.
5. Imahori H., Sakata Y. Eur. J. Org. Chem. 1999;2445-2457.
6. Guldi D.M., Prato M. Acc. Chem. Res. 33:2000;695-703.
7. Gust D., Moore T.A., Moore A.L. Acc. Chem. Res. 34:2001;40-48.
8. Wudl F. J. Mater. Chem. 12:2002;1959-1963.
9. de la Cruz P., Díaz-Ortiz A., García J.J., Gómez-Escalonilla M.J., de la Hoz A., Langa F. Tetrahedron Lett. 40:1999;1587-1590.
10. Langa F., de la Cruz P., Delgado J.L., Gómez-Escalonilla M.J., González-Cortés A., de la Hoz A., López-Arza V. New J. Chem. 26:2002;76-80.
11. Martín N., Sánchez L., Illescas B., Pérez I. Chem. Rev. 98:1998;2527-2548.
12. Guldi D.M. Chem. Commun. 2000;321-327.
13. Langa F., de la Cruz P., Espíldora E., de la Hoz A., Bourdelande J.L., Sánchez L., Martín N. J. Org. Chem. 66:2001;5033-5041.
14. Kordatos K., Da Ros T., Bosi S., Vázquez E., Bergamin M., Cusan C., Pellarini F., Tomberli V., Baiti B., Pantarotto D., Georgakilas V., Spalluto G., Prato M. J. Org. Chem. 66:2001;4915-4920.
15. The synthesis of 1a and 1b has been described previously: Espíldora E., Delgado J.L., de la Cruz P., de la Hoz A., López-Arza V., Langa F. Tetrahedron. 58:2002;5821-5826. The synthetic procedure for 1d and 1e will be described elsewhere.
16. 3) δ 55.8, 114.6, 119.4, 124.0, 125.5, 130.8, 136.2, 137.1, 139.5, 142.3, 142.5, 143.4, 144.2, 144.5, 144.7, 145.4, 145.7, 146.0, 146.2, 146.5, 148.2, 149.9, 144.3, 144.8, 145.1, 145.2, 145.4, 145.7, 145.8, 145.8, 143.2, 147.2, 147.7; MS m/z 989.2, 720.1.
17. Langa F., Gómez-Escalonilla M.J., Diez-Barra E., García-Martínez J.C., de la Hoz A., Rodríguez-López J., González-Cortés A., López-Arza V. Tetrahedron Lett. 42:2001;3435-3438.
18. Vogel's Textbook of Practical Organic Chemistry. 5th ed. 1989;Longman, Essex. p 890.
19. max (nm) ( logε ) 256 (5.2), 317 (4.9), 425 (3.7), 686 (2.5); MS m/z 1064.1, 720.1.
20. A weak peak at around 0.6 V (see Fig. 2) is observed after the first oxidation of the amino group. It does not appear in the first sweep, when starting at 0 V and going first to negative potentials.
21. For a recent review on electronic interactions between donors and [60]fullerene, see: Echegoyen L., Herranz M.A. Guldi D.M., Martín N. Fullerene Electrochemistry. Fullerenes: From Synthesis to Optoelectronic Properties. 2002;Kluwer. Chapter 9.
22. 3) δ 3.05 (s, 6H), 4.28 (s, 5H), 4.43 (s, 2H), 4.78 (s, 2H), 6.83 (d, J =8.8 Hz, 2H), 7.42 (br s, 1H), 7.70 (d, J =8. 8 Hz, 2H), 7.93 (d, J =8.8 Hz, 2H), 8.22 (d, J =8.8 Hz, 2H); MS m/z 1184.1, 720.1.