Chemistry of C84: Separation of three constitutional isomers and optical resolution of D2-C84 by using the 'Bingel-retro-Bingel' strategy

Angewandte Chemie - International Edition

Volumn 38, Issue 11, 1999, Pages 1613-1617

  Crassous, Jeanne ^c   Rivera, José ^d   Fender, Nicolette S ^a   Shu, Lianhe ^a   Echegoyen, Luis ^a   Thilgen, Carlo ^b   Herrmann, Andreas ^b   Diederich, François ^b  

^a UNIVERSITY OF MIAMI   (United States)

^b ETH ZURICH   (Switzerland)

^c UNIVERSITÉ DE LYON   (France)

^d Pontifical Catholic University of Puerto Rico   (Puerto Rico)

Author keywords

Bingel reaction; Circular dichroism; Electrochemistry; Fullerenes

Indexed keywords

CARBON; FULLERENE; FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATION; CYCLIZATION; ELECTROCHEMISTRY; ENANTIOMER; MOLECULAR STABILITY; PURIFICATION;

EID: 0033152119     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1613::AID-ANIE1613>3.0.CO;2-M     Document Type: Article

References (39)

1. F. Diederich, R. Ettl, Y. Rubin, R. L. Whetten, R. Beck, M. Alvarez, S. Anz, D. Sensharma, F. Wudl, K. C. Khemani, A. Koch, Science 1991, 252, 548-551.
2. a) D. E. Manolopoulos, P. W. Fowler, J. Chem. Phys. 1992, 96, 7603-7613;
3. b) B. L. Zhang, C. Z. Wang, K. M. Ho, J. Phys. Chem. 1992, 96, 7183-7185;
4. c) K. Raghavachari, Chem. Phys. Lett. 1992, 190, 397-400;
5. d) D. Bakowies, M. Kolb, W. Thiel, S. Richard, R. Ahlrichs, M. M. Kappes, Chem. Phys. Lett. 1992, 200, 411-417;
6. e) S. Okada, S. Saito, Chem. Phys. Lett. 1996, 252, 94-100.
7. a) K. Kikuchi, N. Nakahara, T. Wakabayashi, S. Suzuki, H. Shiromaru, Y. Miyake, K. Saito, I. Ikemoto, M. Kainosho, Y. Achiba, Nature 1992, 357, 142-145;
8. b) D. E. Manolopoulos, P. W. Fowler, R. Taylor, H. W. Kroto, D. R. M. Walton, J. Chem. Soc. Faraday Trans. 1992, 88, 3117-3118;
9. c) R. Taylor, J. Langley, A. G. Avent, T. J. S. Dennis, H. W. Kroto, D. R. M. Walton, J. Chem. Soc. Perkin Trans. 2 1993, 1029-1036;
10. d) C. Thilgen, F. Diederich, R. L. Whetten, in Buckminsterfullerenes (Eds.: W. E. Billups, M. A. Ciufolini), VCH, New York, 1993, pp. 53-82.
11. a) T. J. S. Dennis, T. Kai, T. Tomiyama, H. Shinohara, Chem. Commun. 1998, 619-620;
12. b) K. M. Allen, T. J. S. Dennis, M. J. Rosseinsky, H. Shinohara, J. Am. Chem. Soc. 1998, 120, 6681-6689.
13. A. L. Balch, A. S. Ginwalla, J. W. Lee, B. C. Noll, M. M. Olmstead, J. Am. Chem. Soc. 1994, 116, 2227-2228.
14. F. Diederich, R. L. Whetten, Acc. Chem. Res. 1992, 25, 119-126.
15. a) "Science and Technology of Fullerene Materials": Y. Achiba, K. Kikuchi, Y. Aihara, T. Wakabayashi, Y. Miyake, M. Kainosho, Mater. Res. Soc. Symp. Proc. 1995, 359, 3-9;
16. b) A. G. Avent, D. Dubois, A. Pénicaud, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1997, 1907-1910.
17. M. Saunders, H. A. Jiménez-Vázquez, R. J. Cross, W. E. Billups, C. Gesenberg, A. Gonzalez, W. Luo, R. C. Haddon, F. Diederich, A. Herrmann, J. Am. Chem. Soc. 1995, 117, 9305-9308.
18. a) C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. 1997, 109, 2362-2374; Angew. Chem. Int. Ed. Engl. 1997, 36, 2269-2280;
19. a) C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. 1997, 109, 2362-2374; Angew. Chem. Int. Ed. Engl. 1997, 36, 2269-2280;
20. b) C. Thilgen, F. Diederich, Top. Curr. Chem. 1999, 199, 135-171.
21. F. Arias, Y. Yang, L. Echegoyen, Q. Lu, S. R. Wilson, in Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials (Eds.: K. M. Kadish, R. S. Ruoff), The Electrochemical Society, Pennington, NJ, 1995, pp. 200-212.
22. R. Kessinger, J. Crassous, A. Herrmann, M. Rüttimann, L. Echegoyen, F. Diederich, Angew. Chem. 1998, 110, 2022-2025; Angew. Chem. Int. Ed. 1998, 37, 1919-1922.
23. R. Kessinger, J. Crassous, A. Herrmann, M. Rüttimann, L. Echegoyen, F. Diederich, Angew. Chem. 1998, 110, 2022-2025; Angew. Chem. Int. Ed. 1998, 37, 1919-1922.
24. J. M. Hawkins, M. Nambu, A. Meyer, J. Am. Chem. Soc. 1994, 116, 7642-7645.
25. a) M. S. Meier, T. F. Guarr, J. P. Selegue, V. K. Vance, J. Chem. Soc. Chem. Commun. 1993, 63-65;
26. b) Y. Yang, F. Arias, L. Echegoyen, L. P. F. Chibante, S. Flanagan, A. Robertson, L. J. Wilson, J. Am. Chem. Soc. 1995, 117, 7801-7804;
27. c) P. L. Boulas, M. T. Jones, R. S. Ruoff, D. C. Lorents, R. Malhotra, D. S. Tse, K. M. Kadish, J. Phys. Chem. 1996, 100, 7573-7579.
28. M. R. Anderson, H. C. Dorn, S. A. Stevenson, S. M. Dana, J. Electroanal. Chem. 1998, 444, 151-154.
29. A. Herrmann, F. Diederich, C. Thilgen, H.-U. ter Meer, W. H. Müller, Helv. Chim. Acta 1994, 77, 1689-1706.
30. A. Herrmann, M. Rüttimann, C. Thilgen, F. Diederich, Helv. Chim. Acta 1995, 78, 1673-1704.
31. R. Taylor, J. Chem. Soc. Perkin Trans. 2 1993, 813-824.
32. E. W. Godly, R. Taylor, Pure Appl. Chem. 1997, 69, 1411-1434.
33. C. Thilgen, A. Herrmann, F. Diederich, Helv. Chim. Acta 1997, 80, 183-199.
34. 84.
35. P. L. Boulas, Y. Zuo, L. Echegoyen, Chem. Commun. 1996, 1547-1548.
36. M. Fanti, G. Orlandi, G. Poggi, F. Zerbetto, Chem. Phys. 1997, 223, 159-168.
37. a) H. Goto, N. Harada, J. Crassous, F. Diederich, J. Chem. Soc. Perkin Trans. 2 1998, 1719-1723;
38. b) G. Orlandi, G. Poggi, F. Zerbetto, Chem. Phys. Lett. 1994, 224, 113-117.
39. M. R. Anderson, H. C. Dorn, P. M. Burbank, J. R. Gibson in Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials (Eds.: K. M. Kadish, R. S. Ruoff), The Electrochemical Society, Pennington, NJ, 1994, pp. 448-456.