Novel cycloaddition reaction of [60]fullerene with carbonyl ylides generated from epoxides

Journal of Organic Chemistry

Volumn 71, Issue 11, 2006, Pages 4346-4348

  Wang, Guan Wu ^a   Yang, Hai Tao ^a   Wu, Ping ^a   Miao, Chun Bao ^a   Xu, Yu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CIS-PRODUCTS; EPOXIDES; PHENYL RING; THERMAL REACTION;

ADDITION REACTIONS; DERIVATIVES; FULLERENES; HEAT TREATMENT; ISOMERS;

CARBONYLATION;

CARBONYL DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; FULLERENE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; YLIDE DERIVATIVE;

ARTICLE; CIS ISOMER; CYCLOADDITION; HEAT TREATMENT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; TRANS ISOMER;

EPOXY COMPOUNDS; FULLERENES; FURANS; MOLECULAR STRUCTURE;

EID: 33646948500     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060427+     Document Type: Article

References (29)

1. For reviews, see: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
2. (b) Hirsch, A. Synthesis 1995, 895.
3. (c) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
4. (d) Hirsch, A. Top. Curr. Chem. 1999, 199, 1.
5. (e) Thilgen, C.; Diederich, F. Top. Curr. Chem. 1999, 199, 135.
6. (f) Yurovskaya, M. A.; Trushkov, I. V. Russ. Chem. Bull., Int. Ed. 2002, 51, 367.
7. (a) Prato, M. Top. Curr. Chem. 1999, 199, 173.
8. (b) Diederich, F.; Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263.
9. (c) Nakamura, E.; Isobe, H. Acc. Chem. Res. 2003, 36, 807.
10. (d) Guldi, D. M.; Zerbetto, F.; Georgakilas, V.; Prato, M. Acc. Chem. Res. 2005, 38, 38.
11. (a) Nair, V.; Sethumadhavan, D.; Sheela, K. C.; Eigendorf, G. K. Tetrahedron Lett. 1999, 40, 5087.
12. (b) Nair, V.; Sethumadhavan, D.; Sheela, K. C.; Nair, S. M.; Eigendorf, G. K. Tetrahedron 2002, 58, 3009.
13. González, R.; Knight, B. W.; Wudl, F. J. Org. Chem. 1994, 59, 7949.
14. Jagerovic, N.; Elguero, J.; Aubagnac, J.-L. J. Chem. Soc., Perkin Trans. 1 1996, 499.
15. For our recent representative papers, see: (a) Wang, G.-W.; Zhang, X.-H.; Zhan, H.; Guo, Q.-X.; Wu, Y.-D. J. Org. Chem. 2003, 68, 6732.
16. (b) Chen, Z.-X.; Wang, G.-W. J. Org. Chem. 2005, 70, 2380.
17. Wang, G.-W.; Li, J.-X.; Li, Y.-J.; Liu, Y.-C. J. Org. Chem. 2006, 71, 680.
18. (d) Wang, G.-W.; Li, F.-B.; Zhang, T.-H. Org. Lett. 2006, 8, 1355-1358.
19. (a) Clawson, P.; Lunn, P. M.; Whiting, D. A. J. Chem. Soc., Perkin. Trans. 1 1990, 159.
20. (b) Yoakim, C.; Goudreau, N.; Mcgibbon, G. A.; Meara, J.; White, P. W.; Ogilvie, W. W. Helv. Chim. Acta 2003, 86, 3427.
21. Ramaiah, D.; Rajadurai, S.; Das, P. K.; George, M. V. J. Org. Chem. 1987, 52, 1082.
22. Robert, A.; Pommeret, J. J.; Marchand, E.; Foucaud, A. Tetrahedron 1973, 29, 463.
23. Meier, K.-R.; Linden, A.; Mlostoñ, G.; Heimgartner, H. Helv. Chim. Acta 1997, 80, 1190.
24. Ruf, S. G.; Dietz, J.; Regitz, M. Tetrahedron 2000, 56, 6259.
25. Kumar, C. V.; Ramaiah, D.; Das, P. K.; George, M. V. J. Org. Chem. 1985, 50, 2818.
26. Kumar, A.; Bhakuni, V. Tetrahedron Lett. 1996, 37, 4751.
27. Foucaud, A.; Bakouetila, M. Synthesis 1987, 854.
28. Adcock, J. L.; Zhang, H. J. Org. Chem. 1995, 60, 1999.
29. Shu, L.-H.; Wang, G.-W.; Wu, S.-H.; Wu, H.-M.; Lao, X.-F. Tetrahedron Lett. 1995, 36, 3871.