Straightforward and versatile synthesis of fullerooxazoles from C60 and carboxamides through radical reactions under mild conditions

Asian Journal of Organic Chemistry

Volumn 2, Issue 1, 2013, Pages 91-97

  Takeda, Youhei ^a   Enokijima, Satoru ^a   Nagamachi, Toshiki ^a   Nakayama, Kazuhisa ^a   Minakata, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Amides; Fullerenes; Halogens; Heterocycles; Radical reactions

Indexed keywords

EID: 84876066502     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201200114     Document Type: Article

References (60)

1. C.-Z. Li, H.-L. Yip, A. K.-Y. Jen, J. Mater. Chem. 2012, 22, 4161;
2. A. M. López, A. Mateo-Alonso, M. Prato, J. Mater. Chem. 2011, 21, 1305;
3. J. L. Delgado, P.-A. Bouit, S. Filippone, M. Á. Herranz, N. Martín, Chem. Commun. 2010, 46, 4853;
4. F. G. Brunetti, R. Kumar, F. Wudl, J. Mater. Chem. 2010, 20, 2934;
5. D. M. Guldi, B. M. Illescas, C. M. Atienza, M. Wielopolski, N. Martín, Chem. Soc. Rev. 2009, 38, 1587;
6. B. C. Thompson, J. M. J. Fréchet, Angew. Chem. 2008, 120, 62; Angew. Chem. Int. Ed. 2008, 47, 58;
7. D. Bonifazi, O. Enger, F. Diederich, Chem. Soc. Rev. 2007, 36, 390;
8. F. Giacalone, N. Martín, Chem. Rev. 2006, 106, 5136;
9. B. M. Illescas, N. Martín, C. R. Chim. 2006, 9, 1038;
10. J. L. Segura, N. Martín, D. M. Guldi, Chem. Soc. Rev. 2005, 34, 31;
11. F. Wudl, J. Mater. Chem. 2002, 12, 1959;
12. N. Martín, L. Sánchez, B. Illescas, I. Pérez, Chem. Rev. 1998, 98, 2527;
13. M. Prato, J. Mater. Chem. 1997, 7, 1097.
14. For comprehensive books and reviews on the reactivity and functionalization methods of fullerenes, see:
15. A. Hirsch, M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim, 2005;
16. Fullerenes: Chemistry, Physics, and Technology (Eds.: K.M. Kadish, R.S. Ruoff), Wiley, New York, 2000;
17. K. Itami, Chem. Rec. 2011, 11, 226;
18. Y. Matsuo, E. Nakamura, Chem. Rev. 2008, 108, 3016;
19. N. Martín, M. Altable, S. Filippone, A. Martín-Domenech, Synlett 2007, 3077;
20. N. Martín, Chem. Commun. 2006, 2093.
21. M. R. Banks, J. I. G. Gadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, D. W. H. Rankin, J. Chem. Soc. Chem. Commun. 1994, 1365.
22. J. Averdung, J. Mattay, D. Jacobi, W. Abraham, Tetrahedron 1995, 51, 2543.
23. M. R. Banks, J. L. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, A. T. Taylor, Tetrahedron Lett. 1994, 35, 9067.
24. H.-L. Hou, X. Gao, J. Org. Chem. 2012, 77, 2553;
25. M. Zheng, F.-F. Li, L. Ni, W.-W. Yang, X. Gao, J. Org. Chem. 2008, 73, 3159.
26. F.-B. Li, T.-X. Liu, G.-W. Wang, J. Org. Chem. 2008, 73, 6417.
27. S. Minakata, Acc. Chem. Res. 2009, 42, 1172.
28. D. D. Tanner, G. C. Gidley, N. Das, J. E. Rowe, A. Potter, J. Am. Chem. Soc. 1984, 106, 5261.
29. Y. Takeda, S. Okumura, S. Minakata, Angew. Chem. 2012, 124, 7924; Angew. Chem. Int. Ed. 2012, 51, 7804;
30. S. Minakata, S. Okumura, T. Nagamachi, Y. Takeda, Org. Lett. 2011, 13, 2966;
31. S. Minakata, I. Sasaki, T. Ide, Angew. Chem. 2010, 122, 1331; Angew. Chem. Int. Ed. 2010, 49, 1309;
32. S. Minakata, Y. Morino, T. Ide, Y. Oderaotoshi, M. Komatsu, Chem. Commun. 2007, 3279;
33. S. Minakata, Y. Morino, Y. Oderaotoshi, M. Komatsu, Chem. Commun. 2006, 3337;
34. S. Minakata, Y. Morino, Y. Oderaotoshi, M. Komatsu, Org. Lett. 2006, 8, 3335.
35. R. Tsuruoka, T. Nagamachi, Y. Murakami, M. Komatsu, S. Minakata, J. Org. Chem. 2009, 74, 1691.
36. S. A. Glover, A. Goosen, R. D. Venter, S. Afr. J. Chem. 1978, 31, 33.
37. See the Chapter6 in Ref.[2a].
38. 60]×100.
39. The characterization methods of fullerooxazoles are well-documented in Ref.[2-6]. For details, see the Supporting Information.
40. G.-W. Wang, C.-Z. Wang, J.-P. Zou, J. Org. Chem. 2011, 76, 6088;
41. W.-W. Yang, Z.-J. Li, X. Gao, J. Org. Chem. 2011, 76, 6067;
42. F. Cheng, Y. Murata, K. Komatsu, Org. Lett. 2002, 4, 2541.
43. For reviews on dumbbell-shaped fullerene derivatives, see:
44. L. Sánchez, M. Á. Herranz, N. Martín, J. Mater. Chem. 2005, 15, 1409;
45. J. L. Segura, N. Martín, Chem. Soc. Rev. 2000, 29, 13.
46. D. M. Guldi, M. Prato, Acc. Chem. Res. 2000, 33, 695.
47. W. Gottardi, Monatsh. Chem. 1975, 106, 1019;
48. W. Gottardi, Monatsh. Chem. 1974, 105, 611.
49. J. W. Bausch, G. K. S. Prakash, G. A. Olah, J. Am. Chem. Soc. 1991, 113, 3205.
50. The formation of 1, 2-addition patterns instead of the formation of D would be unlikely because of significant steric congestion in the resulting radical.
51. R. S. Ruoff, D. S. Tse, R. Malhotra, D. C. Lorents, J. Phys. Chem. 1993, 97, 3379.
52. F. Machui, S. Langner, X. Zhu, S. Abbott, C. J. Brabec, Sol. Energy Mater. Sol. Cells 2012, 100, 138.
53. Although properties have been partially reported in the literature (Ref.[5-7]), to our knowledge, there have been no systematic studies on their physicochemical properties.
54. For detailed data from the UV/vis spectra, cyclic voltammagrams, and TGA, see the Supporting Information.
55. A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Chem. Rev. 2010, 110, 3.
56. d might be ascribed to remaining organic solvents in the samples, although the samples used for the analysis were thoroughly dried before weighing.
57. When cyclic voltammagrams of the sample solutions were measured with wider negative potential windows, the second reduction peaks were electrochemically irreversible.
58. Gaussian09, RevisionA.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
59. The parallel configuration was obtained from initial structures with orthogonal and parallel configurations.
60. Gao and co-workers have reported DFT calculations on 2a, and our results are in good agreement with theirs, see: Z.-J. Li, W.-W. Yang, X. Gao, J. Phys. Chem. A 2011, 115, 6432.