[60]Fullerene (A1,D1)-bisadducts: CD spectra of enantiomers and diastereospecific synthesis

Enantiomer

Volumn 3, Issue 3, 1998, Pages 231-239

  Taki, Masumi ^a   Nakamura, Yosuke ^a   Uehara, Hirofumi ^a   Sato, Mitsuo ^a   Nishimura, Jun ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

60 Fullerene; 60 Fullerene bisadduct; Absolute configuration; Circular dichroism (CD) spectra; Cotton effect; Diastereospecific synthesis

Indexed keywords

2,3 BUTANEDIOL; FULLERENE; FULLERENE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

GOSSYPIUM HIRSUTUM;

EID: 0031770523     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. Prato, M., Bianco, A., Maggini, M., Scorrano, G., Toniolo, C. and Wudl, F. J. Org. Chem. 1993, 58, 5578.
2. Vasella, A., Uhlmann, P.F., Waldraff, C.A.A., Diederich, F. and Thilgen, C. Angew. Chem., Int. Ed. Engl. 1992, 31, 1388.
3. Wilson, S.R., Lu, Q., Cao, J., Wu, Y., Welch, C.J. and Schuster, D.I. Tetrahedron 1996, 52, 5131.
4. Bianco, A., Maggini, M., Scorrano, G., Toniolo, C., Marconi, G., Villani, C. and Prato, M. J. Am. Chem. Soc. 1996, 118, 4072.
5. Schuster, D.I., Cao, J., Kaprinidis, N., Wu, Y., Jensen, A.W., Lu, Q., Wang, H. and Wilson, S.R. J. Am. Chem. Soc. 1996, 118, 5639.
6. Shen, C.K.-F., Chien, K.-M., Juo, C.-G., Her, G.-R. and Luh, T.-Y. J. Org. Chem. 1996, 61, 9242.
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8. Hawkins, J.M., Meyer, A. and Nambu, M. J. Am. Chem. Soc. 1993, 115, 9844.
9. For the nomenclature, see Nakamura, Y., Taki, M. and Nishimura, J. Chem. Lett. 1995, 703.
10. Nakamura, E., Isobe, H., Tokuyama, H. and Sawamura, M. Chem. Commun. 1996, 1747.
11. Nierengarten, J., Gramlich, V., Cardullo, F. and Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101.
12. Taki, M., Sugita, S., Nakamura, Y., Kasashima, E., Yashima, E., Okamoto, Y. and Nishimura, J. J. Am. Chem. Soc. 1997, 119, 926.
13. Generally speaking, only one chiral genetic moiety on the surface of [60]fullerene does not cause any significant Cotton effect in the region above 400 nm. One report shows some Cotton effect in the region above 400 nm: see Maggini, M., Scorrano, G., Bianco, A., Toniolo, C. and Prato, M. Tetrahedron Lett., 1995, 36, 2845, although the highest [θ] value around 630 nm can be read ca. 4000, much smaller than those of 1, 2, and 6.
14. We carefully analyzed the fractions before and after that containing 6b, but no peak corresponding to another enantiomer 6a was detected.
15. 1H NMR spectra. All protons in the cyclohexene region are broadened, indicating the flipping motion of the cyclohexene rings. So we could conclude that there were no significant cyclic bisadducts in the fractions.
16. Mohamadi, F., Richards, N.G.J., Guida, W.C., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickson, T. and Still, W.C. J. Comput. Chem. Soc. 1990, 11, 440.
17. Scrivens, W.A., Bedworth, P.V. and Tour, J.M. J. Am. Chem. Soc. 1992, 114, 7917.
18. Reinhoudt, D.N., Jong, F.D. and Tomassen, H.P.M. Tetrahedron Lett. 1979, 22, 2067.