Progress in the Synthesis and Reaction of Azafullerene

doi:10.6023/cjoc1110183

Abstract

Azafullerene is a very important compound in fullerene family, which has been attracted extensive attention recently because of its unique structure and reactive activities. Recent progress in the preparation and reaction of azafullerene is summarized in this paper. There are three main methods for the synthesis of azafullerene (Wudl’s method, Hirsch’s method and Gan’s method). Azafullerene reactions include free radical reactions and electrophilic aromatic substitution reaction.

Key words: fullerene, carbon-carbon bond cleavage, free radical

Cite this article

Zhang Gaihong. Progress in the Synthesis and Reaction of Azafullerene[J]. Chin. J. Org. Chem., 2012, 32(06): 1010-1023.

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References

[1] Hummelen, J. C.; Bellavia-Lund, C.; Wudl, F. Top. Curr. Chem.1999, 199, 93.

[2] Hirsch, A.; Brettreich, M. Heterofullerenes. Fullerenes, Chemistryand Reactions, 2nd ed.; Wiley-VCH, Weinheim, Germany, 2005,Chapter 12, p. 359.
[3] Hirsch, A.; Nuber, B. Acc. Chem. Res. 1999, 32, 795.

[4] Vostrowsky, O.; Hirsch, A. Chem. Rev. 2006, 106, 5191.

[5] Ewels, C. P. Nano Lett. 2006, 6, 890.

[6] (a) Pradeep, T.; Vijayakrishnan, V.; Santra, A. K.; Rao, C. N. R. J.Phys. Chem. 1991, 95, 10564.(b) Rao, C. N. R.; Pradeep, T.; Seshadri, R.; Govindaraj, A. IndianJ. Chem. 1992, 31A, F27.
[7] Christian, J. F.; Wan, Z.; Anderson, S. L. J. Phys. Chem. 1992, 96,10597.

[8] Averdung, J.; Luftmann, H.; Schlachter, I.; Mattay, J. Tetrahedron1995, 51, 6977.

[9] Lamparth, I.; Nuber, B.; Schick, G.; Skiebe, A.; Groesser, T.;Hirsch, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2257.

[10] Yu, R. Q.; Zhan, M. X.; Cheng, D. D.; Yang, S. Y.; Liu, Z. Y.;Zheng, L. S. J. Phys. Chem. 1995, 99, 1818.

[11] Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F.Science 1995, 269, 1554.

[12] Nuber, B.; Hirsch, A. Chem. Commun. 1996, 1421.
[13] Bellavia-Lund, C.; Keshavarz-K., M.; Collins, T.; Wudl, F. J. Am.Chem. Soc. 1997, 119, 8101.

[14] Zhang, G. H.; Huang, S. H.; Xiao, Z.; Chen, Q.; Gan, L. B.; Wang,Z. M. J. Am. Chem. Soc. 2008, 130, 12614.

[15] Hasharoni, K.; Bellavia-Lund, C.; Keshavarz-K., M.; Srdanov, G.;Wudl, F. J. Am. Chem. Soc. 1997, 119, 11128.

[16] (a) Tagmatarchis, N.; Okada, K.; Tomiyama, T.; Shinohara, H.Synlett 2000, 1761.(b) Tagmatarchis, N.; Forman, G. S.; Shinohara, H. AIP Conf. Proc.2001, 591, 29.

[17] Kobayashi, K.; Nagase, S. Chem. Phys. Lett. 1996, 262, 227.

[18] Stevenson, S.; Rice, G.; Glass, T.; Harich, K.; Cromer, F.; Jordan,M. R.; Craft, J.; Hajdu, E.; Bible, R.; Olmstead, M. M.; Maitra, K.;Fischer, A. J.; Balch, A. L.; Dorn, H. C. Nature 1999, 401, 55.

[19] Akasaka, T.; Okubo, S.; Wakahara, T.; Yamamoto, K.; Kobayashi,K.; Nagase, S.; Kato, T.; Kako, M.; Nakadaira, Y.; Kitayama, Y.;Matsuura, K. Chem. Lett. 1999, 945.
[20] Zuo, T. M.; Xu, L. S.; Beavers, C. M.; Olmstead, M. M.; Fu, W. J.;Crawford, D.; Balch, A. L.; Dorn, H. C. J. Am. Chem. Soc. 2008,130, 12992.

[21] Stevenson, S.; Ling, Y.; Coumbe, C. E.; Mackey, M. A.; Confait,B. S.; Phillips, J. P.; Dorn, H. C.; Zhang, Y. J. Am. Chem. Soc.2009, 131, 17780.

[22] Chen, C. B. Ph.D. Dissertation, University of Science and Technologyof China, Hefei, 2011 (in Chinese).(陈传宝, 博士论文, 中国科技大学, 合肥, 2011.)
[23] Keshavarz-K, M.; Gonzalez, R.; Hicks, R. G.; Srdanov, G.; Srdanov,V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C.;Pavlovich, J.; Wudl, F.; Holczer, K. Nature 1996, 383, 147.

[24] Andreoni, W.; Curioni, A.; Holczer, K.; Prassides, K.;Keshavarz-K, M.; Hummelen, J. C.; Wudl, F. J. Am. Chem. Soc.1996, 118, 11335.

[25] Bellavia-Lund, C.; Gonzalez, R.; Hummelen, J. C.; Hicks, R. G.;Sastre, A.; Wudl, F. J. Am. Chem. Soc. 1997, 119, 2946.

[26] Vougioukalakis, G. C.; Orfanopoulos, M. Tetrahedron Lett. 2003,44, 8649.

[27] Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. J.Org. Chem. 2010, 75, 4124.

[28] Nuber, B.; Hirsch, A. Chem. Commun. 1998, 405.
[29] Hauke, F.; Hirsch, A. Chem. Commun. 1999, 2199.
[30] Hauke, F.; Hirsch, A. Tetrahedron 2001, 57, 3697.

[31] Hauke, F.; Hirsch, A. Liu, S.-G.; Echegoyen, L.; Swartz, A.; Luo,C.; Guldi, D. M. ChemPhysChem 2002, 3, 195.

[32] Hauke, F.; Swartz, A.; Guldi, D. M.; Hirsch, A. J. Mater. Chem.2002, 12, 2088.

[33] Hauke, F.; Atalick, S.; Guldi, D. M.; Mack, J.; Scott, L. T.; Hirsch,A. Chem. Commun. 2004, 766.
[34] Hauke, F.; Hirsch, A. Ph.D. Dissertation, University Erlangen-Nürnberg, Nürnberg, 2003.
[35] Kim, K.-C.; Hauke, F.; Hirsch, A.; Boyd, P. D. W.; Carter, E.;Armstrong, R. S.; Lay, P. A.; Reed, C. A. J. Am. Chem. Soc. 2003,125, 4024.

[36] Vougioukalakis, G. C.; Chronakis, N.; Orfanopoulos, M. Org. Lett.2003, 5, 4603.

[37] (a) Vougioukalakis, G. C.; Orfanopoulos, M. J. Am. Chem. Soc.2004, 126, 15956.(b) Vougioukalakis, G. C.; Hatzimarinaki, M.; Lykakis, I. N.; Orfanopoulos,M. J. Org. Chem. 2006, 71, 829.

[38] Roubelakis, M. M.; Vougioukalakis, G. C.; Nye, L. C.; Drewello,T.; Orfanopoulos, M. Tetrahedron 2010, 66, 9363.

[39] Hauke, F.; Herranz, M. A.; Echegoyen, L.; Angeles, M.; Guldi, D.;Hirsch, A.; Atalik, S. Chem. Commun. 2004, 600.
[40] Hauke, F.; Hirsch, A.; Atalick, S.; Guldi, D. Eur. J. Org. Chem.2005, 1741.
[41] Hauke, F.; Atalick, S.; Guldi, D. M.; Hirsch, A. Tetrahedron 2006,62, 1923.

[42] Reuther, U.; Hirsch, A. Chem. Commun. 1998, 1401.
[43] (a) Birkett, P. R.; Hitchcock, P. B.; Kroto, H. W.; Taylor, R.; Walton,D. R. M. Nature 1992, 357, 479.(b) Birkett, P. R.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.;Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1993,1230.

[44] Hauke, F.; Hirsch, A. Chem. Commun. 2001, 1316.
[45] (a) Lamparth, I.; Maichle-Mössmer, C.; Hirsch, A. Angew. Chem.,Int. Ed. Engl. 1995, 34, 1607.(b) Lamparth, I.; Herzog, A.; Hirsch, A. Tetrahedron 1996, 52,5065.(c) Hirsch, A.; Vostrowsky, O. Eur. J. Org. Chem. 2001, 829.

[46] Shustova, N. B.; Kuvychko, I. V.; Popov, A. A.; Delius, M.; Dunsch,L.; Anderson, O. P.; Hirsch, A.; Strauss, S. H.; Boltalina, O. V.Angew. Chem., Int. Ed. 2011, 50, 5537.

[47] Xu, X. F.; Xing, Y. M.; Shang, Z. F.; Wang, G. C.; Cai, Z. S.; Pan,Y. M.; Zhao, X. Z. Chem. Phys. 2003, 287, 317.

[48] (a) Karfunkel, H. R.; Dressler, T.; Hirsch, A. J. Comput.-AidedMol. Des. 1992, 6, 521.(b) Chen, Z. F.; Zhao, X. Z.; Tang, A. C. J. Phys. Chem. A 1999,103, 10961.(c) Chen, Z. F.; Reuther, U.; Hirsch, A.; Thiel, W. J. Phys. Chem. A2001, 105, 8105.

[49] For one C58N2 isomer (eC) a PM3 HOMO-LUMO gap of 4.22 eV(vs. 6.60 eV for C60) was calculated by using Hyer-Chem.7.5, Hypercube,Inc.
[50] Jiao, H.; Chen, Z.; Hirsch, A.; Thiel, W. Phys. Chem. Chem. Phys.2002, 4, 4916.
[51] Glenis, S.; Cooke, S.; Chen, X.; Labes, M. M. Chem. Mater. 1994,6, 1850.

[52] Reuther, U.; Hirsch, A. Carbon 2000, 38, 1539.

[53] Von Delius, M.; Hauke, F.; Hirsch, A. Eur. J. Org. Chem. 2008,4109.
[54] Pan, B. S.; Zhao, A. D.; Wang, B.; Yang, J. L.; Hou, J. G. Adv.Mater. 2010, 22, 1967.

[55] Zhao, J.; Zeng, C. G.; Cheng, X.; Wang, K. D.; Wang, G. W.;Yang, J. L.; Hou, J. G.; Zhu, Q. S. Phys. Rev. Lett. 2005, 95, 4.
[56] Li, Y. F.; Kaneko, T.; Kong, J.; Hatakeyama, R. J. Am. Chem. Soc.2009, 131, 3412.

[57] Kaneko, T.; Li, Y. F.; Nishigaki, S.; Hatakeyama, R. J. Am. Chem.Soc. 2008, 130, 2714.

[58] Xiang, H.; Liu, D. F.; Wang, Z. W.; Li, Z.; Huang, W. T.; Yang,H.; Guo, Z. X.; Gong, Q. H. Chem. Phys. Lett. 2004, 392, 80.

[59] Gu, F. L.; Chen, Z. F.; Jiao, H. J.; Tian, W. Q.; Aoki, Y.; Thiel, W.;Schleyer, P. V. Phys. Chem. Chem. Phys. 2004, 6, 4566.
[60] Xie, R. H.; Bryant, G. W.; Jensen, L.; Zhao, J. J.; Smith, V. H. J.Chem. Phys. 2003, 118, 8621.

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