Photochemical reaction of the open-cage fullerene derivative with singlet oxygen

Chemistry Letters

Volumn , Issue 9, 2001, Pages 896-897

  Murata, Yasujiro ^a   Komatsu, Koichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035540058     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.896     Document Type: Article

References (19)

1. Y. Rubin, Chem. Eur. J., 3, 1009 (1997).
2. K. M. Creegan, J. L. Robbins, W. K. Robbins, J. M. Millar, R. D. Sherwood, P. J. Tindall, D. M. Cox, A. B. Smith, III, J. P. McCauley, Jr., D. R. Jones, and R. T. Gallagher, J. Am. Chem. Soc., 114, 1103 (1992).
3. J. C. Hummelen, M. Prato, and F. Wudl, J. Am. Chem. Soc., 117, 7003 (1995).
4. a) J. C. Hummelen, B. Knight, J. Pavlovich, R. González, and F. Wudl, Science, 269, 1554 (1995).
5. b) M. Keshavarz-K., R. González, R. G. Hicks, G. Srdanov, V. I. Srdanov, T. G. Collins, J. C. Hummelen, C. Bellavia-Lund, J. Pavlovich, F. Wudl, and K. Holczer, Nature, 383, 147 (1996).
6. G. Scheck, T. Jarrosson, and Y. Rubin, Angew. Chem. Int. Ed., 38, 2360 (1999).
7. Y. Rubin, T. Jarrosson, G.-W. Wang, M. D. Bartberger, K. N. Houk, G. Schick, M. Saunders, and J. Cross, Angew. Chem. Int. Ed., 40, 1543 (2001).
8. Y. Murata, N. Kato, and K. Komatsu, J. Org. Chem., 66 (2001), in press.
9. The related open-cage fullerene derivatives were reported: a) M.-J. Arce, A. L. Viado, Y.-Z. An, S. I. Khan, and Y. Rubin, J. Am. Chem. Soc., 118, 3775 (1996).
10. b) T.-Y. Hsiao, K. C. Santhosh, K.-F. Liou, and C.-H. Cheng, J. Am. Chem. Soc., 120, 12232 (1998).
11. H. Inoue, H. Yamaguchi, T. Suzuki, T. Akasaka, S. Murata, Synlett, 2000, 1178.
12. W. Qian, M. D. Bartberger, S. J. Pastor, K. N. Houk, C. L. Wilkins, and Y. Rubin, J. Am. Chem. Soc., 122, 8333 (2000).
13. H. Inoue, H. Yamaguchi, S. Iwamatsu, T. Uozaki, T. Suzuki, T. Akasaka, S. Nagase, and S. Murata, Tetrahedron Lett., 42, 895 (2001).
14. +), 854.0368; found, 854.0330.
15. All the calculations were conducted by using Gaussian98 program (rev. A.7). M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
16. W. Koch and M. C. Holthausen, "A Chemist's Guide to Density Functional Theory", Wiley-VCH, Weinheim (2000).
17. 13C NMR of 3: δ 198.26 (C=O), 153.52, 152.69, 152.29, 152.21, 152.02, 151.94, 151.90, 151.90, 151.84, 151.81, 151.75, 151.63, 151.37, 151.29, 150.95, 150.92, 150.18, 150.15, 150.08, 150.08, 150.03, 149.84, 149.71, 149.61, 149.56, 148.89, 148.83, 148.76, 148.56 (C-OH), 147.93, 147.32, 147.13, 146.89, 145.97, 145.76, 145.71, 145.51, 145.50, 145.40, 144.86, 144.66, 142.94, 142.63, 142.36, 141.67, 141.29, 141.29, 141.28, 141.27, 141.12, 140.43, 139.43, 139.19, 139.01, 138.87, 137.31, 136.89, 135.42, 135.28, 133.91, 130.62, 129.87 (CH), 129.33 (CH), 129.19 (CH), 128.28 (CH), 119.76 (C=COH), 41.76 (CH).
18. -1.
19. Y. Murata, N. Kato, K. Fujiwara, and K. Komatsu, J. Org. Chem., 64, 3483 (1999).