Opening and closure of the fullerene cage in cis-1-bisimino adducts of C60: The influence of the addition pattern and the addend

Chemistry - A European Journal

Volumn 2, Issue 8, 1996, Pages 935-943

  Schick, Georg ^a   Hirsch, Andreas ^a   Mauser, Harald ^a   Clark, Timothy ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Clusters; Fullerenes; Nitrenes; Regioselectivity; Valence isomerization

Indexed keywords

AM1 CALCULATIONS; CLUSTERS; DENSITY FUNCTIONALS; FULLERENE CAGES; FULLERENE DERIVATIVE; NITRENES; SPECTROSCOPIC CHARACTERIZATION; VALENCE ISOMERIZATION;

CAGES (MINE HOISTS); CHEMICAL BONDS; CHEMICAL MODIFICATION; FULLERENES; ISOMERIZATION; REGIOSELECTIVITY;

ISOMERS;

EID: 0002496765     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020807     Document Type: Article

References (61)

1. a) A. Hirsch, The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994;
2. b) A. Hirsch, Synthesis 1995, 895.
3. F. Dicderich, L. Isaacs, D. Philp, Chem. Soc. Rev. 1994, 243.
4. M. Prato, V. Lucchini, M. Maggini, E. Stimpfl, G. Scorrano, M. Eiermann, T. Suzuki, F. Wudl, J. Am. Chem. Soc. 1993, 115, 8479.
5. M. Prato, Q. Li, F. Wudl, V. Lucchini, J. Am. Chem. Soc. 1993, 115, 1148.
6. M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, D. W. H. Rankin, J. Chem. Soc. Chem. Commun. 1994, 1365.
7. M. R. Banks, J. I. 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.
8. T. Ishida, K. Tanaka, T. Nogami, Chem. Lett. 1994, 561.
9. C. J. Hawker, K. L. Wooley, J. M. J. Frechet, J. Chem. Soc. Chem. Commun. 1994, 925.
10. M. Yan, S. X. Cai, J. F. W. Keana, J. Org. Chem. 1994, 59, 5951.
11. J. Averdung, H. Luftmann, J. Mattay, K.-U. Claus, W. Abraham, Tetrahedron Lett. 1995, 36, 2957.
12. M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, J. A. S. Parkinson, D. W. H. Rankin, A. T. Taylor, J. Chem. Soc. Chem. Commun. 1995, 887.
13. M. R. Banks. J. I. G. Cadogan. I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, A. T. Taylor, J. Chem. Soc. Chem. Commun. 1995, 88.
14. G. Schick, T. Grösser, A. Hirsch, J. Chem. Soc. Chem. Commun. 1995, 2289.
15. a) E. Vogel, "Aromaticity", Spec. Publ. No. 21, The Chemical Society, London, 1967, 113
16. b) E. Vogel, Pure Appl. Chem. 1969, 20, 237;
17. c) E. Vogel, Isr. J. Chem. 1980, 20, 215;
18. d) E. Vogel, Pure Appl. Chem. 1993, 65, 143.
19. a) K. Raghavachari, C. Sosa, Chem. Phys. Lett. 1993, 209, 223;
20. b) F. Diederich, L. Isaacs, D. Philp, J. Chem. Soc. Perkin Tians. 2, 1994, 391.
21. R. C. Haddon, Science 1993, 261, 1545.
22. a) H. L. Anderson, C. Boudon, F. Diederich, J.-P. Gisselbrecht, M. Gross, P. Seiler, Angew. Chem. 1994, 106, 1691;
23. Angew. Chem. Int. Ed. Engl. 1994, 33, 1628;
24. b) J. Osterodt, M. Nieger, F. Vögtle, J. Chem. Soc. Chem. Commun. 1994, 1607;
25. c) E. F. Paulus, C. Bingel, Acta Crystallogr. C 1995. 51, 143;
26. d) I. Lamparth, C. Maichle-Mössmer. A. Hirsch, Angew. Chem. 1995, 107, 1755;
27. Angew. Chem. Int. Ed. Engl. 1995, 34, 1607;
28. e) A. Hirsch, B. Nuber, E Djojo. unpublished results;
29. f) Y. Rubin. S. Khan, D. I. Freedberg. C. Yeretzian. J. Am. Chem. Soc. 1993, 115, 344;
30. g) F. Diederich, U. Jonas, V. Gramlich, A. Herrmann, H. Ringsdorf, C. Thilgen, Helv. Chim. Acta 1993, 76, 2445-2553;
31. h) P. Belik, A. Gügel, A. Kraus, J. Spickermann, V. Enkelmann, G. Frank, K. Müllen, Adv. Mater. 1993, 5, 854;
32. i) P. Seiler, A. Herrmann, F. Diederich, Helv. Chim. Acta 1995, 78, 344.
33. -1. N. Matsuzawa, D. A. Dixon, T. Fukunaga, J. Phys. Chem. 1992, 96, 7594.
34. a) T. Grösser, M. Prato, V. Luahini, A. Hirsch, F. Wudl, Angew. Chem. 1995, 107, 1462;
35. Angew. Chem. Int. Ed. Engl. 1995, 34, 1343;
36. b) L.-L. Shiu, K.-M. Chien, T.-Y. Liu, T.-I. Lin, G.-R. Her, T.-Y. Luh, J. Chem. Soc. Chem. Commun. 1995, 1159;
37. c) G.-X. Dong, J.-S. Li, T.-H. Chang, ibid. 1995, 1725.
38. a) A. Hirsch. I. Lamparth, H. R. Karfunkel, Angew. Chem. 1994, 106, 453;
39. Angew. Chem. Int. Ed. Engl. 1994, 33, 437;
40. b) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385;
41. c) I. Lamparth, C. Maichle-Mössmer, A. Hirsch, Angew. Chem. 1995, 107, 1755;
42. Angew. Chem. Int. Ed. Engl. 1995, 34, 1607.
43. d) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, in press;
44. e) L. Isaacs, R. F. Haldimann, F. Diederich, Angew. Chem. 1994, 106, 2435;
45. Angew. Chem. Int. Ed. Engl. 1994, 33, 2434.
46. I. Lamparth, B. Nuber, G. Schick, A. Skiebe, T. Gro̊sser, A. Hilsch, Angew. Chem. 1995, 107, 2473;
47. Angew. Chem. Int. Ed. Engl. 1995, 34, 2257.
48. H. Prinzbach, M. Breuninger, B. Gallenkamp, R. Schwesinger, D. Hunkler, Angew. Chem. 1975, 87, 350.
49. A. Hirsch. B. Nuber, unpublished results.
50. 60 radical are located in positions 2.4, and 6; J. R. Morton, K. F. Preston, P. J. Krusic, S. A. Hill, E. Wasserman, J. Phys. Chem. 1992, 96, 3576.
51. M. Breuninger, B. Gallenkamp, K.-H. Müller, H. Fritz, H. Prinzbach, J. J. Daley, P. Schönholzer, Angew. Chem. 1979, 91, 1030.
52. H.-J. Altenbach, H. Stegelmeier, M. Wilhelm, B. Voss. J. Lex, E. Vogel, Angew. Chem. 1979, 91, 1028.
53. A. Hirsch, E Djojo, A. Herzog, I. Lamparth, unpublished results.
54. We thank Prof. E. Vogel for sending us the corresponding spectroscopic data as well as for helpful discussions.
55. E. Vogel, W. Püttmann. W. Duchatsch, T. Schieb, H. Schmickler, J. Lex, Angew. Chem. 1996, 98, 727.
56. E. Vogel, F. Kuebart, J. A. Marco, R. Andree, H. Günther, R. Aydin, J. Am. Chem. Soc. 1983, 105, 6982.
57. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy. J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
58. HyperChem 4.5, Hypercube, Inc., Waterloo, Ontario N2L 3X2, Canada, 1995.
59. VAMP5.6, G. Rauhut. A. Alex, J. Chandrasekhar, T. Steine, W. Sauer, B. Beck, M. Hutter, T. Clark, Oxford Molecular, Magdalen Centre, Oxford Science Park, Standford-on-Thames, Oxford OX44GA, England, 1995.
60. P. J. Stevens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch. J. Phys. Chem. 1994, 98, 11623.
61. Gaussian 94, Revision B.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, G. Johnson, M. A. Robb. J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery. K. Raghavachari, M. A. Al-Lahan, V. G. Nanayakkara, M. Challacombe, C. Y. Peng. P. Y. Ayala, W. Cheng, M. W. Wong, J. L. Andres, E. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, - P. Stewart, M. Head-Gordon, C. Gonzales, L. A. Pople, Gaussian Inc., Pittsburg PA. 1995.