Approaches to open fullerenes: A 1,2,3,4,5,6-hexaadduct of C60

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4525-4528

  Chuang, Shih Ching ^a   Clemente, Fernando R ^a   Khan, Saeed I ^a   Houk, K N ^a   Rubin, Yves ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750042917     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061707e     Document Type: Article

References (29)

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19. 3 has been postulated; see: Tajima, Y.; Takeuchi, K. J. Org. Chem. 2002, 67, 1696-1698.
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24. See the Supporting Information.
25. w = 0.335.
26. Chuang, S.-C.; Rubin, Y. A full account of the reactivity of compound 1 toward cyclopropanation (Bingel reaction) will be reported elsewhere.
27. Irle, S.; Rubin, Y.; Morokuma, K. J. Phys. Chem. A 2002, 106, 680-688.
28. Calculations were performed using Gaussian 98, revision A.9: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
29. Preliminary results indicate that reductive opening of both epoxy bridges occurs under McMurry conditions: Chuang, S.-C.; Rubin, Y. Unpublished results.