Evaluation of an intramolecular approach for the synthesis of the elusive C58N2 heterofullerene family

European Journal of Organic Chemistry

Volumn , Issue 24, 2008, Pages 4109-4119

  Von Delius, Max ^a   Hauke, Frank ^a   Hirsch, Andreas ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

1,3 Dipolar cycloaddition; Azides; Fullerenes; Heterofullerenes; Molecular modelling

Indexed keywords

EID: 53749103961     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800423     Document Type: Article

References (49)

1. W. Kraetschmer, L. D. Lamb, K. Fostiropoulos, D. R. Huffman, Nature 1990, 347, 354-358.
2. H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, R. E. Smalley, Nature 1985, 318, 162-163.
3. J. C. Hummelen, B. Knight, J. Pavlovich, R. Gonzalez, F. Wudl, Science 1995, 269, 1554-1556.
4. a) I. Lamparth, B. Nuber, G. Schick, A. Skiebe, T. Groesser, A. Hirsch, Angew. Chem. Int. Ed. Engl. 1995, 34, 2257-2259;
5. b) B. Nuber, A. Hirsch, Chem. Commun. 1996, 1421-1422.
6. J. Averdung, H. Luftmann, I. Schlachter, J. Mattay, Tetrahedron 1995, 51, 6977-6982.
7. For reviews see: a) O. Vostrowsky, A. Hirsch, Chem. Rev. 2006, 106, 5191-5207;
8. b) J. C. Hummelen, C. Bellavia-Lund, F. Wudl, Top. Curr. Chem. 1999, 199, 93-134;
9. c) A. Hirsch, B. Nuber, Acc. Chem. Res. 1999, 32, 795-804.
10. a) C. Bellavia-Lund, M. Keshavarz-K., T. Collins, F. Wudl, J. Am. Chem. Soc. 1997, 119, 8101-8102;
11. b) C. Bellavia-Lund, R. Gonzalez, J. C. Hummelen, R. G. Hicks, A. Sastre, F. Wudl, J. Am. Chem. Soc. 1997, 119, 2946-2947;
12. c) A. Gruss, K.-P. Dinse, A. Hirsch, B. Nuber, U. Reuther, J. Am. Chem. Soc. 1997, 119, 8728-8729;
13. d) T. Pichler, M. Knupfer, M. S. Golden, S. Haffner, R. Friedlein, J. Fink, W. Andreoni, A. Curioni, M. Keshavarz-K., C. Bellavia-Lund, A. Sastre, J.-C. Hummelen, F. Wudl, Phys. Rev. Lett. 1997, 78, 4249-4252;
14. e) S. Haffner, T. Pichler, M. Knupfer, B. Umlauf, R. Friedlein, M. S. Golden, J. Fink, M. Keshavarz-K., C. Bellavia-Lund, A. Sastre, J. C. Hummelen, F. Wudl, Eur. Phys. J. B 1998, 1, 11-17;
15. f) K.-C. Kim, F. Hauke, A. Hirsch, P. D. W. Boyd, E. Carter, R. S. Armstrong, P. A. Lay, C. A. Reed, J. Am. Chem. Soc. 2003, 125, 4024-4025;
16. g) C. M. Brown, E. Beer, C. Bellavia, L. Cristofolini, R. Gonzalez, M. Hanfland, D. Haeusermann, M. Keshavarz-K., K. Kordatos, K. Prassides, F. Wudl, J. Am. Chem. Soc. 1996, 118, 8715-8716;
17. h) T. Kaneko, Y. Li, S. Nishigaki, R. Hatakeyama, J. Am. Chem. Soc. 2008, 130, 2714-2715.
18. a) B. Nuber, A. Hirsch, Chem. Commun. 1998, 405-406;
19. b) U. Reuther, A. Hirsch, Chem. Commun. 1998, 1401-1402;
20. c) F. Hauke, A. Hirsch, Chem. Commun. 1999, 2199-2200;
21. d) O. V. Boltalina, T. Drewello, A. Hirsch, T. J. D. Jorgensen, V. Y. Markov, U. Reuther, Proc. Electrochem. Soc. 1999, 99-12, 462-471;
22. e) F. Hauke, A. Hirsch, Chem. Commun. 2001, 1316-1317.
23. a) S. Glenis, S. Cooke, X. Chen, M. M. Labes, Chem. Mater. 1994, 6, 1850-1853;
24. b) S. Glenis, S. Cooke, X. Chen, M. M. Labes, Synth. Met. 1995, 70, 1313-1316.
25. U. Reuther, A. Hirsch, Carbon 2000, 38, 1539-1549.
26. X. Xu, Y. Xing, Z. Shang, G. Wang, Z. Cai, Y. Pan, X. Zhao, Chem. Phys. 2003, 287, 317-333.
27. a) H. R. Karfunkel, T. Dressler, A. Hirsch, J. Comput.-Aided Mol. Des. 1992, 6, 521-535;
28. b) Z. Chen, X. Zhao, A. Tang, J. Phys. Chem. A 1999, 103, 10961-10968;
29. c) Z. Chen, U. Reuther, A. Hirsch, W. Thiel, J. Phys. Chem. A 2001, 105, 8105-8110.
30. 60) was calculated by using Hyer-Chem. 7.5, Hypercube, Inc.
31. [6] or: M. Keshavarz-K., R. Gonzalez, R. G. Hicks, G. Srdanov, V. I. Srdanov, T. G. Collins, J. C. Hummelen, C. Bellavia-Lund, J. Pavlovich, F. Wudl, K. Holczer, Nature 1996, 383, 147-150.
32. For an X-ray structure of a similar triazoline adduct, see: B. Nuber, F. Hampel, A. Hirsch, Chem. Commun. 1996, 1799-1800.
33. T. Groesser, M. Prato, V. Lucchini, A. Hirsch, F. Wudl, Angew. Chem. Int. Ed. Engl. 1995, 34, 1343-1345.
34. U. Reuther, A. Hirsch, unpublished results.
35. PM3 method, Spartan '06, version 1.1.0, Wavefunction, Inc.
36. a) W. J. Hehre, R. Ditchfield, L. Radom, J. A. Pople, J. Am. Chem. Soc. 1970, 92, 4796-4801;
37. b) P. George, M. Trachtman, C. W. Bock, A. M. Brett, Theor. Chim. Acta 1975, 38, 121-129;
38. c) W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio molecular orbital theory, John Wiley & Sons, New York, 1986.
39. a) P. J. Kocienski, Protecting groups, Thieme, Stuttgart, 2005;
40. b) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999.
41. H. R. Henze, V. B. Duff, W. H. Matthews Jr, J. W. Melton, E. O. Forman, J. Am. Chem. Soc. 1942, 64, 1222-1223.
42. G. A. Olah, S. Yu, G. Liang, G. D. Matseescu, M. R. Bruce, D. J. Donovan, M. Arvanaghi, J. Org. Chem. 1981, 46, 571-577.
43. E. Wedekind, Ber. Dtsch. Chem. Ges. 1903, 36, 1383-1386.
44. E. J. Corey, J. L. Gras, P. Ulrich, Tetrahedron Lett. 1976, 17, 809-812.
45. D. A. Goff, R. N. Harris III, J. C. Bottaro, C. D. Bedford, J. Org. Chem. 1986, 51, 4711-4714.
46. A. G. Shipov, I. A. Savost'yanova, Y. I. Baukov, Zh. Obshch. Khim. 1989, 59, 1204-1205.
47. C. Gomez, B. Macia, V. J. Lillo, M. Yus, Tetrahedron 2006, 62, 9832-9839.
48. a) L. Isaacs, A. Wehrsig, F. Diederich, Helv. Chim. Acta 1993, 76, 1231-1250;
49. b) W. A. Scrivens, A. M. Cassell, B. L. North, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 6939-6940.