Selective Preparation of Oxygen-Rich [60]Fullerene Derivatives by Stepwise Addition of tert-Butylperoxy Radical and Further Functionalization of the Fullerene Mixed Peroxides

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2442-2453

  Huang, Shaohua ^a   Xiao, Zuo ^a   Wang, Fudong ^a   Gan, Liangbing ^a,b   Zhang, Xiang ^a   Hu, Xiangqing ^a   Zhang, Shiwei ^a,c   Lu, Mujian ^a   Pan, Qinqi ^a   Xu, Li ^a,d  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c PEKING UNIVERSITY   (China)

^d BEIJING INSTITUTE OF MICROCHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; CRYSTAL STRUCTURE; DERIVATIVES; OXYGEN; PEROXIDES; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS;

FUNCTIONALIZATIONS; LIGHT IRRADIATION;

FULLERENES;

EPOXIDE; FULLERENE DERIVATIVE; OXYGEN; PEROXIDE; RADICAL; TERT BUTYL HYDROPEROXIDE; TERT BUTYLPEROXY RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; LIGHT; REACTION ANALYSIS; REACTION TIME; SPECTROSCOPY;

EID: 12144291591     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049974q     Document Type: Article

References (69)

1. Thorp, H. H.; Karlsbeck J. Electroanal. Chem. 1991, 314, 363-370.
2. Wood, J. M.; Kahr, B.; Hoke, S. H., II; Dejarme, L.; Cooks, R. G.; Ben-Amotz, D. J. Am. Chem. Soc. 1991, 113, 5907-5908.
3. Heymann, D.; Bachilo, S. M.; Weisman, R. B.; Cataldo, F.; Fokkens, R. H. ; Nibbering, N. M. M.; Vis, R. D.; Chibante, L. P. F. J. Am. Chem. Soc. 2000, 122, 11473-11479 and references therein.
4. Chiang, L. Y.; Swirczewski, J.; Chang, S. H.; Chowdhury, S. K.; Cameron, S.; Creegan, K. J. Chem. Soc., Chem. Commun 1992, 1791-1793.
5. Chiang, L. Y.; Upasani, R. B.; Swirczewski, J. Am. Chem. Soc. 1992, 114, 10154-10157.
6. Chiang, L. Y.; Wang, L. Y.; Swirczewski, J. W.; Miller, G.; Soled, S.; Cameron, S. J. Org. Chem. 1994, 59, 3960-3968.
7. Wilson, S. R.; Wu, Y. H. J. Am. Chem. Soc. 1993, 115, 10334-10337.
8. Kreegan, K. M.; Robbins, K. L.; Robbins, W. K.; Millar, J. M.; Sherwood, R. D.; Tindall, P. J.; Cox, D. M.; Smith, A. B., III; McCauley, J. P., Jr.; Jones, D. R.; Gallagher, R. T. J. Am. Chem. Soc. 1992, 114, 1103-1105.
9. (b) Elemes, Y.; Silverman, S. K.; Sheu, C.; Kao, M.; Foote, C. S.; Alvarez, M. M.; Whetten, R. Angew Chem., Int. Ed. Engl. 1992, 31, 351-353.
10. Weisman, R. B.; Heymann, D.; Bachilo, S. M. J. Am. Chem. Soc. 2001, 123, 9720-9721.
11. Balch, A. L.; Costa, D. A.; Noll, B. C.; Olmstead, M. M. J. Am. Chem. Soc. 1995, 117, 8926-8932.
12. (a) Hamano, T.; Okuda, K.; Mashino, T.; Hirobe, M. J. Chem. Soc., Chem. Commun. 1995, 1537-1538.
13. (b) Fusco, C.; Seraglia, R.; Curci, R.; Lucchini, V. J. Org. Chem. 1999, 64, 8363-8368.
14. (c) Tajima, Y.; Takeuchi, K. J. Org. Chem. 2002, 67, 1696-1698.
15. Meier, M. S.; Kiegiel, J. Org. Lett. 2001, 3, 1717-1719.
16. (a) Avent, A. G.; Birkett, P. R.; Darwish, A. D.; Houlton, S.; Taylor, R.; Thomson, K. S. T.; Wei, X. W. J. Chem. Soc., Perkin Trans. 2 2001, 782-786.
17. (b) Wang, G.; Shu, L.; Wu, S.; Wu, H.; Lao, X. J. Chem. Soc., Chem. Commun. 1995, 1071-1072.
18. Zhang, W.; Gan, L. B.; Huang, C. H. Chin. J. Chem. 1998, 16, 478-480.
19. Gan, L. B.; Huang, S. H.; Zhang, X. A.; Zhang, A. X.; Cheng, B. C.; Cheng, H.; Li, X. L.; Shang, G. J. Am. Chem. Soc. 2002, 124, 13384-13385.
20. (a) Krusic, P. J.; Wasserman, E.; Keizer, P. N.; Morton, J. R.; Preston, K. F. Science 1991, 254, 1183-1185.
21. (b) Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Plumitallo, A. J. Org. Chem. 1996, 61, 3327-3331.
22. Taylor, R. Synlett 2000, 776-793. Taylor, R. Chem. Eur. J. 2001, 7, 4074-4083.
23. Taylor, R. Synlett 2000, 776-793. Taylor, R. Chem. Eur. J. 2001, 7, 4074-4083.
24. Corey, E. J.; Yu, J. Q. Org. Lett. 2002, 4, 2727-2730 and references therein.
25. Murahashi, S. I.; Komiya, N.; Oda, Y.; Kuwabara, T.; Naota, T. J. Org. Chem. 2000, 65, 9186-9193.
26. (a) Barton, D. H. R.; Le Gloahec, V. N.; Patin, H.; Launay, F. New J. Chem. 1998, 22, 559-563.
27. (b) Barton, D. H. R.; Le Gloahec, V. N. Tetrahedron 1998, 54, 15457-15468.
28. Kharasch, M. S.; Fono, A.; Nudenberg, W.; Bischof, B. J. Org. Chem. 1952, 17, 207-220.
29. Jones, C. M.; Burkitt, M. J. J. Chem. Soc., Perkin Trans. 2 2002, 2044-2051.
30. (a) Milas, N. A.; Plesnicar, B. J. Am. Chem. Soc. 1968, 90, 4450-4453.
31. (b) Traylor, T. G.; Fann, W. P.; Bandyopadhyay, D. J. Am. Chem. Soc. 1989, 111, 8009-8010.
32. Hirsch, A. Top. Curr. Chem. 1999, 99, 1-89.
33. Caron, C.; Subramanian, R.; D'Souza, F.; Kim, J.; Kutner, W.; Jones, M. T.; Kadish K. M. J. Am. Chem. Soc. 1993, 115, 8505-8506.
34. Clare, B. W.; Kepert, D. L. THEOCHEM 2003, 612 (3), 211-231.
35. It could be prepared, see Kadish, K. M.; Gao, X.; Caemelbecke, E. V.; Hirasaka, T.; Suenobu, T.; Fukuzumi, S. J. Phys. Chem. Soc. A 1998, 102, 3898-3906.
36. Murata, Y.; Shiro, M.; Komatsu, K. J. Am. Chem. Soc. 1997, 119, 8117-8118.
37. (a) Schick, G.; Kampe, K. D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 19, 2023-2024.
38. (b) Isobe, H.; Tomita, N.; Nakamura, E. Org. Lett. 2000, 2, 3663-3665.
39. (c) Sawamura, M.; Iikura, H.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 12850-12851.
40. (a) Al-Matar, H.; Abdul-Sada, A. K.; Avent, A. G.; Taylor, R. Org. Lett. 2001, 3, 1669-1671.
41. (b) Al-Matar, H.; Abdul-Sada, A. K.; Avent, A. G.; Fowler, P. W.; Hitchcock, P. B.; Rogers, K. M.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 2002, 53-58.
42. Avent, A. G.; Birkett, P. R.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1998, 2153-2154.
43. Fabio, R. D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590.
44. Bender, M. L. J. Am. Chem. Soc. 1953, 75, 5986-5990.
45. (a) Birkett, P. R.; Avent, A. G.; Darwish, A. D.; Hahn, I.; Kroto, H. W. ; Langley, G. J.; O'Loughlin, J.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Perkin Trans. 2, 1997, 1121-1125.
46. (b) Birkett, P. R.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Tetrahedron 1996, 52, 5235-5246.
47. (a) Avent, A. G.; Abdul-Sada, A. K.; Clare, B. W.; Kepert, D. L.; Street, J. M.; Taylor, R. Org. Biomol. Chem. 2003, 1, 1026-1033.
48. (b) Darwish, A. D.; Avent, A. G.; Street, J. M.; Taylor, R. Org. Biomol. Chem. 2003, 1, 1764-1768.
49. (c) Wei, X. W.; Avent, A. G.; Boltalina, O. V.; Darwish, A. D.; Fowler, P. W.; Sandall, J. P. B.; Street, J.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 2002, 41-46.
50. (d) Wei, X. W.; Darwish, A. D.; Boltalina, O. V.; Hitchcock, P. B.; Street, J. M.; Taylor, R. Angew. Chem., Int. Ed. 2001, 40, 2989-2992.
51. (a) Cramail, C.; Degueil-Castaing, M.; Maillard, B. J. Org. Chem. 2001, 66, 3492-3494.
52. (b) Cramay, C.; Degueil-Castaing, M.; Maillard, B. J. Chem. Soc., Perkin Trans. 1 1999, 3573-3577.
53. dos Santos, R. A. B.; Muralha, V. S. F.; Correia, C. F.; Simoes, J. A. M. J. Am. Chem. Soc. 2001, 123, 12670-12674.
54. Deng, J. P.; Ju, D. D.; Her, G. R.; Mou, C. Y.; Chen, C. J.; Lin, Y. Y.; Han, C. C. J. Phys. Chem. 1993, 97, 11575-11577.
55. (a) Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Hohnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9298.
56. (b) Krusic, P. J.; Roe, D. C.; Johnston, E.; Morton, J. R.; Preston, K. F. J. Phys. Chem. 1993, 97, 1736-1738.
57. Obtained with pure CS2.
58. For an overview of this topic, see: Rubin, Y. Top. Curr. Top. 1999, 99, 67-91.
59. Kepert, D. L.; Clare, B. W. Inorg. Chim. Acta 2002, 327, 41-53.
60. Hummelen, J. C.; Prato, M.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 7003-7004.
61. (a) Swern, D. Organic Peroxides; Wiley-Interscience: New York, 1972; (1981 reprint by Robert E. Krieger Publishing Co., Inc.); Vol. III, Chapter I, pp 37-42.
62. (b) Ando W. Organic Peroxides; John Wiley & Sons: New York, 1992; Chapter 3, pp 174-183.
63. (b) Schalley, C. A.; Schroder, D.; Schwarz, H. Helv. Chim. Acta 1995, 78, 1999-2010.
64. (a) Hiatt, R.; Irwin, K. C.; Gould, C. W. J. Org. Chem. 1968, 33, 1421-1428.
65. (b) Hiatt, R.; Irwin, K. C.; Gould, C. W. J. Org. Chem. 1968, 33, 1430-1435.
66. Aldrich Condensed Phase Library; Aldrich: Milwaukee, WI.
67. Murata, Y.; Murata, M.; Komatsu, K. Chem. Eur. J. 2003, 9, 1600-1609.
68. Iwamatsu, S.; Ono, F.; Murata, S. J. Chem. Soc., Chem. Commun. 2003, 1268-1269.
69. Al-Matar, H.; Abdul-Sada, A. K.; Avent, A. G.; Taylor, R. Org. Lett. 2001, 3, 1669-1671.