Formation of an effective opening within the fullerene core of C60 by an unusual reaction sequence

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2360-2363

  Schick, Georg ^a   Jarrosson, Thibaut ^a   Rubin, Yves ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Azides; Cycloadditions; Diels Alder reactions; Fullerenes; Semiempirical calculations

Indexed keywords

CYCLOHEXANE; FULLERENE DERIVATIVE; MACROCYCLIC COMPOUND; OXYGEN; TRIAZOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HYDROGEN BOND; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033549729     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2360::AID-ANIE2360>3.0.CO;2-V     Document Type: Article

References (46)

1. a) Y. Rubin, Chem. Eur. J. 1997, 3, 1009-1016;
2. b) Y. Rubin, Top. Curr. Chem. 1999, 199, 67-91.
3. a) J. C. Hummelen, M. Prato, F. Wudl, J. Am. Chem. Soc. 1995, 117, 7003-7004;
4. 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, 1159-1160;
5. c) C. K. F. Shen, H. Yu, C.-G. Juo, K.-M. Chien, G.-R. Her, T.-Y. Luh, Chem. Eur. J. 1997, 3, 744-748;
6. d) G. X. Dong, J. S. Li, T. H. Chan, J. Chem. Soc. Chem. Commun. 1995, 1725-1726;
7. e) P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor, D. R. M. Walton, J. Chem. Soc. Chem. Commun. 1995, 1869-1870;
8. f) M. J. Arce, A. L. Viado, Y. Z. An, S. I. Khan, Y. Rubin, J. Am. Chem. Soc. 1996, 118, 3775-3776;
9. g) G. Schick, A. Hirsch, H. Mauser, T. Clark, Chem. Eur. J. 1996, 2, 935-943.
10. a) A. Hirsch, The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994;
11. b) A. Hirsch, Top. Curr. Chem. 1999, 199, 1-65.
12. a) M. Prato, C. Li, F. Wudl, V. Lucchini, J. Am. Chem. Soc. 1993, 115, 1148-1150;
13. b) T. Grösser, M. Prato, V. Lucchini, A. Hirsch, F. Wudl, Angew. Chem. 1995, 107, 1462-1464; Angew. Chem. Int. Ed. Engl. 1995, 34, 1343-1345;
14. b) T. Grösser, M. Prato, V. Lucchini, A. Hirsch, F. Wudl, Angew. Chem. 1995, 107, 1462-1464; Angew. Chem. Int. Ed. Engl. 1995, 34, 1343-1345;
15. c) B. Nuber, F. Hampel, A. Hirsch, Chem. Commun. 1996, 1799-1800;
16. d) J. Averdung, J. Mattay, Tetrahedron 1996, 52, 5407-5420;
17. e) 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, 1365-1366.
18. a) Y. Rubin, S. Khan, D. I. Freedberg, C. Yeretzian, J. Am. Chem. Soc. 1993, 115, 344-345;
19. b) Y. Z. An, G. A. Ellis, A. L. Viado, Y. Rubin, J. Org. Chem, 1995, 60, 6353-6361;
20. c) Y. Z. An, A. L. Viado, M. J. Arce, Y. Rubin, J. Org. Chem. 1995, 60, 8330-8331.
21. In deference to Prof. Emmanuel Vogel's life-long work on bridged annulenes, we propose that this nomenclature be followed over the current IUPAC and CAS systems; see a) E. Vogel, W. Pretzer, W. A. Böll, Tetrahedron Lett. 1965, 3613-3617; b) F. Gerson, G. Gescheidt, U. Buser, E. Vogel, J. Lex, M. Zehnder, A. Riesen, Angew. Chem. 1989, 101, 938-940; Angew. Chem. Int. Ed. Engl. 1989, 28, 902-904; c) J. A. Marco, J. F. Sanz, E. Vogel, B. Schwartzkopff-Fischer, H. Schmickler, J. Lex, Tetrahedron Lett. 1990, 31, 999-1002; see also ref. [2c].
22. In deference to Prof. Emmanuel Vogel's life-long work on bridged annulenes, we propose that this nomenclature be followed over the current IUPAC and CAS systems; see a) E. Vogel, W. Pretzer, W. A. Böll, Tetrahedron Lett. 1965, 3613-3617; b) F. Gerson, G. Gescheidt, U. Buser, E. Vogel, J. Lex, M. Zehnder, A. Riesen, Angew. Chem. 1989, 101, 938-940; Angew. Chem. Int. Ed. Engl. 1989, 28, 902-904; c) J. A. Marco, J. F. Sanz, E. Vogel, B. Schwartzkopff-Fischer, H. Schmickler, J. Lex, Tetrahedron Lett. 1990, 31, 999-1002; see also ref. [2c].
23. In deference to Prof. Emmanuel Vogel's life-long work on bridged annulenes, we propose that this nomenclature be followed over the current IUPAC and CAS systems; see a) E. Vogel, W. Pretzer, W. A. Böll, Tetrahedron Lett. 1965, 3613-3617; b) F. Gerson, G. Gescheidt, U. Buser, E. Vogel, J. Lex, M. Zehnder, A. Riesen, Angew. Chem. 1989, 101, 938-940; Angew. Chem. Int. Ed. Engl. 1989, 28, 902-904; c) J. A. Marco, J. F. Sanz, E. Vogel, B. Schwartzkopff-Fischer, H. Schmickler, J. Lex, Tetrahedron Lett. 1990, 31, 999-1002; see also ref. [2c].
24. In deference to Prof. Emmanuel Vogel's life-long work on bridged annulenes, we propose that this nomenclature be followed over the current IUPAC and CAS systems; see a) E. Vogel, W. Pretzer, W. A. Böll, Tetrahedron Lett. 1965, 3613-3617; b) F. Gerson, G. Gescheidt, U. Buser, E. Vogel, J. Lex, M. Zehnder, A. Riesen, Angew. Chem. 1989, 101, 938-940; Angew. Chem. Int. Ed. Engl. 1989, 28, 902-904; c) J. A. Marco, J. F. Sanz, E. Vogel, B. Schwartzkopff-Fischer, H. Schmickler, J. Lex, Tetrahedron Lett. 1990, 31, 999-1002; see also ref. [2c].
25. H. Schmidbaur, R. Hager, B. Huber, G. Müller, Angew. Chem. 1987, 99, 354-356; Angew. Chem. Int. Ed. Engl. 1987, 26, 338-340.
26. H. Schmidbaur, R. Hager, B. Huber, G. Müller, Angew. Chem. 1987, 99, 354-356; Angew. Chem. Int. Ed. Engl. 1987, 26, 338-340.
27. See the Supporting Information.
28. A number of crystallization attempts for X-ray crystallographic determination were performed with the three series of derivatives described in this work. So far, only microcrystalline material has been obtained.
29. 60 in toluene or ODCB at temperatures up to 180°C gave new products in neither case.
30. Y. Rubin, P. S. Ganapathi, A. Franz, Y.-Z. An, W. Qian, R. Neier, Chem. Eur. J. 1999, 5, No. 11.
31. a) W. Oppolzer, Angew. Chem. 1977, 89, 10-24; Angew. Chem. Int. Ed. Engl. 1977, 16, 10-23;
32. a) W. Oppolzer, Angew. Chem. 1977, 89, 10-24; Angew. Chem. Int. Ed. Engl. 1977, 16, 10-23;
33. b) G. Brieger, J. N. Bennett, Chem. Rev. 1980, 80, 63-97;
34. c) A. G. Fallis, Can. J. Chem. 1984, 62, 183-234;
35. d) D. Craig, Chem. Soc. Rev. 1987, 16, 187-238.
36. For the chemistry of 1,4-diaminobutadienes, see a) R. Sustmann, K. Lücking, G. Kopp, M. Rese, Angew. Chem. 1989, 101, 1701-1704; Angew. Chem. Int. Ed. Engl. 1989, 28, 1713-1715; b) D. H. R. Barton, C. C. Dawes, G. Franceschi, M. Foglio, S. V. Ley, P. D. Magnus, W. L. Mitchell, A. Temperelli, J. Chem. Soc. Perkin Trans. 1 1980, 643-647; c) R. R. Schmidt, A. Wagner, Synthesis 1981, 273-275.
37. For the chemistry of 1,4-diaminobutadienes, see a) R. Sustmann, K. Lücking, G. Kopp, M. Rese, Angew. Chem. 1989, 101, 1701-1704; Angew. Chem. Int. Ed. Engl. 1989, 28, 1713-1715; b) D. H. R. Barton, C. C. Dawes, G. Franceschi, M. Foglio, S. V. Ley, P. D. Magnus, W. L. Mitchell, A. Temperelli, J. Chem. Soc. Perkin Trans. 1 1980, 643-647; c) R. R. Schmidt, A. Wagner, Synthesis 1981, 273-275.
38. For the chemistry of 1,4-diaminobutadienes, see a) R. Sustmann, K. Lücking, G. Kopp, M. Rese, Angew. Chem. 1989, 101, 1701-1704; Angew. Chem. Int. Ed. Engl. 1989, 28, 1713-1715; b) D. H. R. Barton, C. C. Dawes, G. Franceschi, M. Foglio, S. V. Ley, P. D. Magnus, W. L. Mitchell, A. Temperelli, J. Chem. Soc. Perkin Trans. 1 1980, 643-647; c) R. R. Schmidt, A. Wagner, Synthesis 1981, 273-275.
39. For the chemistry of 1,4-diaminobutadienes, see a) R. Sustmann, K. Lücking, G. Kopp, M. Rese, Angew. Chem. 1989, 101, 1701-1704; Angew. Chem. Int. Ed. Engl. 1989, 28, 1713-1715; b) D. H. R. Barton, C. C. Dawes, G. Franceschi, M. Foglio, S. V. Ley, P. D. Magnus, W. L. Mitchell, A. Temperelli, J. Chem. Soc. Perkin Trans. 1 1980, 643-647; c) R. R. Schmidt, A. Wagner, Synthesis 1981, 273-275.
40. 2 upon workup cannot be entirely excluded. However, singlet oxygen is generated in close to quantitative yields upon excitation of most fullerene derivatives by visible light: J. L. Anderson, Y. Z. An, Y. Rubin, C. S. Foote, J. Am. Chem. Soc. 1994, 116, 9763-9764, and ref. [5c].
41. a) C. S. Foote, S. Wexler, J. Am. Chem. Soc. 1964, 86, 3879-3880;
42. b) C. S. Foote, S. Wexler, W. Ando, R. Higgins, J. Am. Chem. Soc. 1968, 90, 975-981;
43. c) T. Sato, I. Moritani, M. Matsuyama, Tetrahedron Lett. 1969, 5113-5116;
44. d) Y. Nakaraida, T. Nomura, S. Kanouchi, R. Sato, C. Kabuto, H. Sakurai, Chem. Lett. 1983, 209-212;
45. e) G. Rio, J. Berthelot, Bull. Soc. Chim. Fr. 1970, 1509-1511;
46. f) G. Rio, J. Berthelot, Bull. Soc. Chim. Fr. 1971, 2938-2942.