New route for [60[fullerene functionalisation in [4 + 2] cycloaddition reaction using indene

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 285-288

  Puplovskis, Austris ^a   Kacens, Janis ^a   Neilands, Ojars ^a  

^a RIGA TECHNICAL UNIVERSITY   (Latvia)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0031030671     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02293-9     Document Type: Article

References (26)

1. For a recent review, see: (a) Hirsch, A. Synthesis 1995, 895.
2. (b) Taylor, R; Walton, D.R.M. Nature 1993, 363, 685.
3. (c) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243.
4. (d) Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994.
5. Belik, P.; Gügel, A; Spickermann, J.; Müllen, K. Angew. Chem., Int. Ed Engl. 1993, 32, 78.
6. (a) Diederich, F.; Ulrich, J.; Gramlich, V.; Herrmann, A.; Ringsdorf; H.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2445.
7. (b) Bidell, W.; Douthwaite, RE.; Green, M.L.H.; Stephens, A.H.H.; Turner, J.F.C. J.Chem. Soc., Chem. Commun. 1994, 1641.
8. (c) Belik, P.; Gügel, A; Kraus, A.; Walter, M.; Müllen, K. J. Org. Chem. 1995, 60, 3307.
9. (a) Gügel, A.; Müllen, K. Chromatographia 1993, 37, 387.
10. (b) Belik, P.; Gügel, A; Kraus, A.; Spikermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854.
11. (a) Tago, T.; Minowa, T.; Okada, Y.; Nishimura, J. Tetrahedron Lett. 1993, 8461.
12. (b) Gügel, A; Kraus, A.; Spickermann, J.; Belik, P.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 559.
13. (c) Iyoda, M.; Sultana, F.; Saski, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929.
14. (d) Zhang, X.; Foote, C.S. J. Org. Chem. 1994, 59, 5235.
15. (e) Tomioka, H.; Ichihashi, M.; Yamamoto, K. Tetrahedron Lett. 1995, 5371.
16. Illescas, B.; Martin, N.; Seoane, C.; Cruz, de la P.; Langa, F.; Wudl, F. Tetrahedron Lett. 1995, 8307.
17. (a) Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M. Chem. Lett. 1992, 2333.
18. (b) Rotello, V.M.; Howard, J.B.; Yadav, T.; Conn, M.M.; Viani, E.; Giovane, L.M.;Lafleur, A.L. Tetrahedron Lett. 1993, 1561.
19. (c) Meidine, M.F.; Roers, R.; Langley, J.; Avent, A.G.; Darwish, A.D.; Firth, S.; Kroto, H.W.; Taylor, R.; Walton, D.R.M. J.Chem. Soc., Chem. Commun. 1993, 1342.
20. (d) Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M. J.Chem. Soc., Chem. Commun. 1993, 1296.
21. (e) Pang, L.S.K.; Wilson, M.A. J. Phys. Chem. 1993, 97, 6761.
22. (f) Giovane, L.M.; Barco, J.W.; Yadav, T.; Lafleur, A.L.; Marr, J.A.; Howard, J.B.; Rotello, V.M. J. Phys. Chem. 1993, 97, 8560.
23. Alder, K.; Pascher, F. Ber. 1942, 75, 1501.
24. In the case of larger excess of indene or of longer period of the reaction was, the yield of mono-adduct decreased.
25. 3 as relaxation agent), δ 156.24(2). 154.89(2), 147.19(2), 146.27(2), 146.14(2), 146.05(4), 145.98(4), 145.67(2), 145.38(4), 145.20(2), 145.08(2), 144.57(2), 144.38(2), 143.06(2), 142.85(1), 142.64(2), 142.50(2), 142.38(1), 142.27(2), 142.17(2), 142.05(2), 141.97(2), 141.87(2), 141.58(1), 141.47(1), 140.16(2), 139.67(2), 137.60(2), 137.37(2).
26. OX for 1: (benzonitrile with TBAP as supporting electrolyte, glass carbon electrode, Ag/AgCl reference electrode, scan rate 200 mV/s) -0.56/-0.48, -0.97/-0.89, -1.54/-1.45; for [60]fullerene: -0.45/-0.32, -0.87/-0.75, -1.35/-1.25, -1.85/-1.72.