Addition of carbene to the equator of C70 to produce the most stable C71H2 isomer: 2aH-2(12)a-homo(C7o-D 5h(6))[5,6]fullerene

Angewandte Chemie - International Edition

Volumn 49, Issue 5, 2010, Pages 962-966

  Li, Bao ^a   Shu, Chunying ^a   Lu, Xin ^b   Dunsch, Lothar ^c   Chen, Zhongfang ^d   Dennis, T John S ^e   Shi, Zhiqiang ^a   Jiang, Li ^a   Wang, Taishan ^a   Xu, Wei ^a   Wang, Chunru ^a  

^a PEKING UNIVERSITY   (China)

^b XIAMEN UNIVERSITY   (China)

^c IFW Dresden ^*  (Germany)

^d UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^e QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Carbenes; Fullerenes; Gas phase reactions; NMR spectroscopy; Regioselectivity

Indexed keywords

ACTIVATION BARRIERS; CARBENES; GAS-PHASE REACTIONS; NMR SPECTROSCOPY; STABLE ISOMERS; SYNTHETIC METHODS; THEORETICAL STUDY;

ISOMERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE INTERFACES; REGIOSELECTIVITY;

FULLERENES;

EID: 75749117940     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905263     Document Type: Article

References (39)

1. R. Taylor, C. R. Chim. 2006, 9, 982-1000.
2. a) M. Prato, F. Wudl in The Chemistry of Fullerenes, Vol.4 (Ed.: R. Taylor), World Scientific, New York, 1995, pp. 151-173;
3. b) A. Hirsch, M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim, 2005.
4. R. Taylor. J. P. Hare. A. K. Abdulsada, H. W. Kroto. J. Chem. Soc. Chem. Commun. 1990, 1423-1424.
5. R. C. Haddon, Science 1993, 261, 1545-1550.
6. C. Bellavia-Lund, F. Wudl, J. Am. Chem. Soc. 1997, 119, 943-946.
7. A. B. Smith III, R. M. Strongin, L. Brard, G. T. Furst, W. J. Romanow, K. G. Owens, R. J. Goldschmidt, J. Chem. Soc. Chem. Commun. 1994. 2187-2188.
8. A. B. Smith III, R. M. Strongin, L. Brard, G. T. Furst, W. J. Romanow, K. G. Owens, R. J. Goldschmidt, R. C. King, J. Am. Chem. Soc. 1995, 117, 5492-5502.
9. A. F. Kiely, R. C. Haddon, M. S. Meier, J. P. Selegue, C. P. Brock, B. O. Patrick, G. W. Wang, Y. S. Chen, J. Am. Chem. Soc. 1999, 121, 7971-7972.
10. T Sternfeld. C. Thilgen, R. E. Hoffman, M. D. C. Heras, F. Diederich, F. Wudl, L. T. Scott, J. Mack, M. Rabinovitz, J. Am. Chem. Soc. 2002, 124, 5734-5738.
11. T. Sternfeld, R. E. Hoffman, C. Thilgen, F. Diederich, M. Rabinovitz, J. Am. Chem. Soc. 2000, 122, 9038-9039.
12. For reviews, see: a) Z. Chen. R. B. King, Chem. Rev. 2005. 105, 3613-3642;
13. b) M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153-1183.
14. M. Bühl, Chem. Eur. J. 1998, 4, 734-739.
15. a) Z. Chen, S. Nagase, A. Hirsch, R. C. Haddon, W. Thiel, P. von R. Schleyer. Angew. Chem. 2004, 116. 1578-1580;
16. Angew. Chem. Int. Ed. 2004, 43, 1552-1554;
17. b) J. Zhao, Z. F. Chen, Z. Zhou. H. Park, P. von R. Schleyer. J. P. Lu. ChemPhysChem 2005, 6, 598-601.
18. T. Umeyama, N. Tezuka, M. Fujita, Y. Matano, N. Takeda, K. Murakoshi, K. Yoshida, S. Isoda, H. Imahori, J. Phys Chem. C 2007, 111, 9734-9741.
19. a) F. Diederich. C. Thilgen. Science 1996, 271, 317-323:
20. b) A. Hirsch in Fullerenes and Related Structures: Fullerenes and Related Structures, Springer, Berlin, 1999, Vol.199, pp. 1-65;
21. R. Taylor, Lecture Notes on Fullerene Chemistry: A Handbook for Chemists, Imperial College Press, London, 1999, pp. 137-163.
22. S. Huang. Z. Xiao. F. Wang, J. Zhou. G. Yuan, S. Zhang, Z. Chen, W. Thiel, P. von R. Schleyer. X. Zhang, X. Hu. B. Chen, L. Gan, Chem. Eur. J. 2005, 11, 5449-5456.
23. a) G. Schick, A. Hirsch, H. Mauser, T. Clark, Chem. Eur. J. 1996, 2, 935-943;
24. b) E. Kemner, A. Hirsch, F. Zerbetto, J. Phys Chem. A 2004, 108, 135-7138:
25. O. V. Boltalina, B. de La Vaissière, P. W. Fowler, A. Yu. Lukonin, A. K. Abdul-Sada, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 22000, 2212-2216;
26. R. Taylor, J. Fluorine Chem. 2004. 125, 359-368;
27. e) A. A. Goryunkov et al., Dalton Trans. 2008, 6886 (see the Supporting Information).
28. Y.-Z. Tan, Z.-J. Liao. Z.-Z. Qian. R.-T. Chen, X. Wu. H. Liang, X. Han, F. Zhu, S.-J. Zhou, Z. Zheng, X. Lu, S.-Y. Xie, R.-B. Huang, L.-S. Zheng, Nat. Mater. 2008, 7, 790-794.
29. C.-R. Wang, Z.-Q. Shi, L.-J. Wan, X. Lu, L. Dunsch, C.-Y. Shu, Y.-L. Tang, H. Shinohara, J. Am. Chem. Soc 2006, 128, 6605-6610.
30. T. Akasaka, E. Mitsuhida, W. Ando, K. Kobayashi, S. Nagase, J. Am. Chem. Soc 1994, 116, 2627-2628.
31. 2 isomer has a closed three-membered ring, instead of an open structure; see: Q. Teng, X. Zhao, Z.-S. Cai, A. C. Tang, Int. J. Quantum Chem. 1997, 61, 815-822.
32. H. Jiao, N. J. R. van Eikemma Hommes, P. von R. Schleyer. Org. Lett. 2002, 4, 2393-2396.
33. D. Heymann, S. M. Bachilo, R. B. Weisman, J. Am. Chem. Soc. 2002, 124, 6317-6323.
34. W. Krätschmer, L. D. Lamb, K. Fostiropoulos, D. R. Huffman, Nature 1990, 347, 354-356.
35. a) T. Sternfeld, C. Thilgen, Z. Chen, S. Siefken, P. von R. Schleyer. W. Thiel. F. Diederich. M. Rabinovitz, J. Org. Chem. 2003, 68, 4850-4854;
36. b) C. Shu, T. Cai, L. Xu, T. Zuo, J. Reid, K. Harich, H. C. Dorn, H. W. Gibson, J. Am. Chem. Soc. 2007, 129, 15710-15717.
37. C. Shu, W. Xu, C. Slebodnick, H. Champion, W. Fu, J. E. Reid, H. Azurmendi, C. Wang, K. Harich, H. C. Dorn, H. W. Gibson, Org. Lett. 2009. 11. 1753-1756.
38. A. D. Kent, T. M. Shaw. S. Vonmolnar, D. D. Awschalom. Science 1993, 262, 1249-1252.
39. Gaussian 98 (Revision A.11.l): M. J. Frisch et al. (see the Supporting Information).