Unusual reactions of C60 with aldehydes in the presence of aqueous ammonia

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4031-4034

  Komori, Akifumi ^a   Kubota, Masayuki ^a   Ishida, Takayuki ^a   Niwa, Haruki ^a   Nogami, Takashi ^a  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030014660     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00754-X     Document Type: Article

References (26)

1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
2. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
3. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
4. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
5. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
6. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693; Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243-255; Hirsch, A. The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994; Śliwa, W. Fullerene Sci. Technol. 1995, 3, 243-281; Diederich, F.; Thilgen, C. Science 1996, 271, 317-323; Symposium-in-Print on Fullerene Chemistry ed by Smith, A. B. Tetrahedron 1996, 52, 4925-5262.
7. Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. J. Am. Chem. Soc. 1991, 114, 7301-7302.
8. Meier, M. S.; Poplawska, M. J. Org. Chem. 1993, 58, 4524-4525.
9. Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798-9799; Zhang, X.; Willems, M.; Foote, C. S. Tetrahedron Lett. 1993, 34, 8187-8188.
10. Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798-9799; Zhang, X.; Willems, M.; Foote, C. S. Tetrahedron Lett. 1993, 34, 8187-8188.
11. Wilson, S. R.; Wang, Y.; Cao, J.; Tan, X. Tetrahedron Lett. 1996, 37, 775-778.
12. Kawasumi, M.; Ishida, T.; Nogami, T. Fullerene Sci. Technol. in press.
13. -1 (broad).
14. 2 trans-1a could not be detected because they were buried under those of cis-1a.
15. 10 indicated the total steric energies of 407.22 and 408.18 kcal/mol for cis-and trans-1a, respectively.
16. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134.
17. 5
18. Chen, J.; Cai, R.-F.; Huang, Z.-E.; Wu, H.-M.; Jiang, S.-K.; Shao, Q.-F. J. Chem. Soc., Chem. Commun. 1995, 1553-1554.
19. Possible adducts are, for example, (Formula presented)
20. Averdung, J.; Albrecht, E.; Lauterwein, J.; Luftmann, H.; Mattay, J.; Mohn, H.; Müller, W. H.; ter Meer, H.-U. Chem. Ber. 1994, 127, 787-789; Iyoda, M.; Sultana, F.; Komatsu, M. Chem. Lett. 1995, 1133-1134.
21. Averdung, J.; Albrecht, E.; Lauterwein, J.; Luftmann, H.; Mattay, J.; Mohn, H.; Müller, W. H.; ter Meer, H.-U. Chem. Ber. 1994, 127, 787-789; Iyoda, M.; Sultana, F.; Komatsu, M. Chem. Lett. 1995, 1133-1134.
22. Carey, F. A.; Sundberg, R. J. "Advanced Organic Chemistry, Part A," Plenum, New York (1990), Chap. 12.
23. Skiebe, A.; Hirsch, A.; Klos, H.; Gotschy, B. Chem. Phys. Lett. 1994, 220, 138-140; Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; Grüner, G.; Thompson, J. D. Science 1991, 253, 301-303; Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024. For photoinduced electron transfer reactions, see Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y.-P. J. Chem. Soc., Chem. Commun. 1995, 2225-2226 and references cited therein.
24. Skiebe, A.; Hirsch, A.; Klos, H.; Gotschy, B. Chem. Phys. Lett. 1994, 220, 138-140; Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; Grüner, G.; Thompson, J. D. Science 1991, 253, 301-303; Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024. For photoinduced electron transfer reactions, see Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y.-P. J. Chem. Soc., Chem. Commun. 1995, 2225-2226 and references cited therein.
25. Skiebe, A.; Hirsch, A.; Klos, H.; Gotschy, B. Chem. Phys. Lett. 1994, 220, 138-140; Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; Grüner, G.; Thompson, J. D. Science 1991, 253, 301-303; Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024. For photoinduced electron transfer reactions, see Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y.-P. J. Chem. Soc., Chem. Commun. 1995, 2225-2226 and references cited therein.
26. Skiebe, A.; Hirsch, A.; Klos, H.; Gotschy, B. Chem. Phys. Lett. 1994, 220, 138-140; Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; Grüner, G.; Thompson, J. D. Science 1991, 253, 301-303; Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023-2024. For photoinduced electron transfer reactions, see Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y.-P. J. Chem. Soc., Chem. Commun. 1995, 2225-2226 and references cited therein.