Electrochemical studies of seven regioisomers of tris[di(ethoxycarbonyl)methanol][60]fullerence: Umpolung of regiochemistry in retro-bingel reactions and walk-on-the-sphere rearrangements

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4994-5000

  Echegoyen, Lourdes E ^a   Djojo, Francis D ^b   Hirsch, Andreas ^b   Echegoyen, Luis ^a  

^a UNIVERSITY OF MIAMI   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTROLYSIS; ISOMER; ISOMERISM; REACTION ANALYSIS; TEMPERATURE; THERMODYNAMICS;

EID: 0034637587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000524h     Document Type: Article

References (34)

1. (a) Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
2. (b) Hirsch, A. Top. Curr. Chem. 1999, 199, 1-65.
3. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
4. Thilgen, C.; Herrmann, A.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1997, 80, 2238-2276.
5. Hirsch, A.; Lamparth, I.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 437-438.
6. Hirsch, A.; Lamparth, I.; Grösser, T.; Karfunkel, H. R. J. Am. Chem. Soc. 1994, 116, 9385-9386.
7. Lamparth, I.; Maichele-Mössmer, C.; Hirsch, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1607-1609.
8. Hirsch, A.; Lamparth, I.; Schick, G. Liebigs. Ann. 1996, 1725-1734.
9. Djojo, F.; Herzog, A.; Lamparth, I.; Hampel, F.; Hirsch, A. Chem. Eur. J. 1996, 2, 1537-1547 and references therein.
10. Djojo, F.; Hirsch, A. Chem. Eur. J. 1998, 4, 344-356.
11. Hawkins, J. M.; Meyer, A.; Nambu, M. J. Am. Chem. Soc. 1993, 115, 9844-9845.
12. Hawkins, J. M.; Meyer, A.; Lewis, T. A.; Bunz, U.; Nunlist, R.; Ball, G. E.; Ebbesen, T.; Tanigaki, K. J. Am. Chem. Soc. 1992, 114, 7954-7955.
13. Diederich, F.; Kessinger, R. Acc. Chem. Res. 1999, 32, 537-545.
14. Fagan, P. J.; Calabrese, J. C.; Malone, B. Acc. Chem. Res. 1992, 25, 134-142.
15. Murata, Y.; Shiro, M.; Komatsu, K. J. Am. Chem, Soc. 1997, 119, 8117-8118.
16. Isaacs, L.; Haldimann, R. F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2339-2342.
17. Schwenninger, R.; Müller, T.; Kräutler, B J. Am. Chem. Soc. 1997, 119, 9317-9318.
18. Bingel, C. Chem. Ber. 1993, 126, 1957-1959.
19. Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255.
20. Isaacs, L.; Diederich, F.; Haldimann, R. F. Helv. Chim. Acta 1997, 2, 317-342.
21. Rapenne, G.; Crassous, J.; Collet, A.; Echegoyen, L.; Diederich, F. Chem. Commun. 1999, 1121-1122.
22. Diederich, F.; Gomez-Lopez, M. Chimia 1998, 52, 551-556.
23. Prato, M. J. Mater. Chem. 1997, 7, 1097-1109.
24. Friedman, S. H.; De Camp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6510-6512.
25. Dugan, L. L.; Turetsky, D. M.; Du, C.; Lobner, D.; Wheeler, M.; Almli, C. R.; Shen, C. K.-F.; Luh, T.-Y.; Choi, D. W.; Lin, T.-S. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 9434-9439.
26. Chen, B.-X.; Wilson, S. R.; Das, M.; Coughlin, D. J.; Erlanger, B. F. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10809-10813.
27. Kessinger, R.; Gomez-Lopez, M.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Echegoyen, L.; Diederich, F. J. Am. Chem. Soc. 1998, 120, 8545-8546.
28. Kessinger, R.; Crassous, J.; Herrmann, A.; Rüttimann, M.; Echegoyen, L.; Diederich, F. Angew. Chem., Int. Ed. 1998, 37, 1919-1922.
29. Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Herrmann, A.; Rüttimann, M.; Crassous, J.; Cardullo, F.; Echegoyen, L.; Diederich, F. J. Am. Chem. Soc. 1998, 120, 7860-7868.
30. Crassous, J.; Rivera, J.; Fender, N. S.; Shu, L.; Echegoyen, L.; Thilgen, C.; Herrmann, A.; Diederich, F. Angew. Chem. 1999, 111, 1716-1721.
31. Djojo, F.; Hirsch, A. Eur. J. Org. Chem. 1999, 3027-3039.
32. HYPERCHEM 4.5; Hypercube, 1995, 419 Phillip Street, Waterloo, Ontario, N2L3X2 (Canada).
33. Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 2445-2457.
34. Boulas, P. L.; Zuo, Y.; Echegoyen, L. J Chem. Soc., Chem. Commun. 1996, 1547-1548.