Highly regioselective transformation of out/out-equatorial bis(formylmethano)[60]fullerenes: Construction of dissymmetric [60]fullerene-centered triads

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4759-4765

  Ito, Hiroshi ^a   Ishida, Yasuhiro ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONALIZATION; DISSYMMETRIC [60]FULLERENE-CENTERED TRIADS; EQUATORIAL BIS(FORMYLMETHANO); REGIOSELECTIVE TRANSFORMATION;

AMINES; CONDENSATION; ISOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

FULLERENES;

[60]FULLERENE; AROMATIC AMINE; BIS(ALPHA FORMYLSULFONIUM YLIDE); BIS(FORMYLMETHANO)[60]FULLERENE DERIVATIVE; FORMYL GROUP; FULLERENE DERIVATIVE; FUNCTIONAL GROUP; IMINE; MONOMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY; SYNTHESIS; TRANSFORMATION REACTION;

AMINES; BENZENE DERIVATIVES; CARBON ISOTOPES; COLORING AGENTS; FULLERENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

EID: 33745444831     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060110+     Document Type: Article

References (34)

1. Kadish, K. M.; Ruo, R. S. Fullerenes: Chemistry, Physics, and Technology; Wiley-Interscience: New York, 2000.
2. (a) Nierengarten, J.-F.; Gramlich, V.; Cardullo, D.-C. F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103.
3. (b) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J. P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238-2276.
4. Diederich, F.; Kessinger, R. Acc. Chem. Res. 1999, 32, 537-545.
5. (a) Taki, M.; Takigami, S.; Watanabe, Y.; Nakamura, Y.; Nishimura, J. Polym. J. 1997, 29, 1020-1022.
6. (b) Kessinger, R.; Thilgen, C.; Mordasini, T.; Diederich, F. Helv. Chim. Acta 2000, 83, 3069-3096.
7. (c) Hino, T.; Hamada, M.; Kinbara, K.; Saigo, K. Chem. Lett. 2002, 728-729.
8. (d) Nierengarten, J.-F. New J. Chem. 2004, 28, 1177-1191.
9. (a) Hirsh, A.; Lamparth, I.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 437-438.
10. (b) Schick, G.; Hirsh, A.; Mauser, H.; Clark, T. Chem. Eur. J. 1996, 2, 935-943.
11. (c) Lu, Q.; Schuster, D. I.; Wilson, S. R. J. Org. Chem. 1996, 61, 4764-4768.
12. (d) Nakamura, Y.; O-kawa, K.; Matsumoto, M.; Nishimura, J. Tetrahedron 2000, 56, 5429-5434.
13. (e) Nakamura, Y.; Takano, N.; Nishimura, T.; Yashima, E.; Sato, M.; Kudo, T.; Nishimura, J. Org. Lett. 2001, 3, 1193-1196.
14. 60 bisadducts by the tether-directed method, see: (a) Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926-932.
15. (b) Reference 2a.
16. (c) Nakamura, Y.; O-kawa, K.; Nishimura, J. Bull. Chem. Soc. Jpn. 2003, 76, 865.
17. (d) Nakamura Y.; Suzuki, M.; Imai, Y.; Nishimura, J. Org. Lett. 2004, 6, 2797-2799.
18. (e) Sergeyev, S.; Schar, M.; Seiler, P.; Lukoyanova, O.; Echegoyen, L.; Diederich, F. Chem. Eur. J. 2005, 11, 2284-2294.
19. Ito, H.; Ishida, Y.; Saigo, K. Tetrahedron Lett. 2005, 46, 8757-8760.
20. Hamada, M.; Hino, T.; Kinbara, K.; Saigo, K. Tetrahedron Lett. 2001, 42, 5069-5071.
21. Ito, H.; Ishida, Y.; Saigo, K. Tetrahedron Lett. 2006, 47, 3095-3098.
22. See Supporting Information.
23. 60, see: Taylor, R. J. Chem. Soc., Perkin Trans. 2 1993, 813-824.
24. Ball, G. E.; Burley, G. A.; Chaker, L.; Hawkins, B. C.; Williams, J. R.; Keller, P. A.; Pyne, S. G. J. Org. Chem. 2005, 70, 8572-8574.
25. Higuchi, M.; Kimoto, A.; Shiki, S.; Yamamoto, K. J. Org. Chem. 2000, 65, 5680-5684.
26. (b) Higuchi, M.; Shiki, S.; Yamamoto, K. Org. Lett. 2000, 2, 3079-3082.
27. 4/DABCO, an irreversible nature of the imination reaction was proved in our system, by using other substrates; in the transformation of the remaining formyl group of 3b with an aromatic amine other than that used for the first imination. the products due to the scrambling of the amino groups were not observed.
28. 60-porphyrin hybrids, see: (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771-11782.
29. (b) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Roder, B. Chem. Commun. 1998, 1981-1982.
30. (c) Tashiro, K.; Aida, T.; Zheng, J. Y.; Kinbara, K.; Saigo, K.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 1999, 121, 9477-9478.
31. Luo, C.; Guldi, D. M.; Imahori, H.; Tamaki, K.; Sakata, K. J. Am. Chem. Soc. 2000, 122, 6535-6551.
32. Imahori, H.; Guldi, D. M.; Tamaki, K.; Yoshida, Y.; Luo, C. P.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6617-6628.
33. Herranz, M. A.; Illescas, B.; Martin, N.; Luo, C. P.; Guldi, D. M. J. Org. Chem. 2000, 65, 5728-5738.
34. 2 = p-MPhe) could by separated from each other by HPLC. See Experimental Section.