Synthesis, properties, and reactions of a stable carbanion derived from alkynyldihydrofullerene: 1-Octynyl-C60 carbanion

Tetrahedron

Volumn 52, Issue 14, 1996, Pages 5077-5090

  Murata, Yasujiro ^a   Motoyama, Kiyoto ^a   Komatsu, Koichi ^a   Wan, Terence S M ^b  

^a KYOTO UNIVERSITY   (Japan)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029874021     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00115-9     Document Type: Article

References (23)

1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Olah, G. A.; Bucsí, I.; Aniszfeld, R.; Prakash, G. K. S. Carbon 1992, 30, 1203-1211. Hirsch, A. The Chemistry of the Fullerenes; Georg Thieme Verlag, Stuttgart, 1994. See also Boyd, P. D. W.; Bhyrappa, P.; Paul, P.; Stinchcombe, J.; Bolskar, R. D.; Sun, Y.; Reed, C. A. J. Am. Chem. Soc. 1995, 117, 2907-2914 and references cited therein.
2. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Olah, G. A.; Bucsí, I.; Aniszfeld, R.; Prakash, G. K. S. Carbon 1992, 30, 1203-1211. Hirsch, A. The Chemistry of the Fullerenes; Georg Thieme Verlag, Stuttgart, 1994. See also Boyd, P. D. W.; Bhyrappa, P.; Paul, P.; Stinchcombe, J.; Bolskar, R. D.; Sun, Y.; Reed, C. A. J. Am. Chem. Soc. 1995, 117, 2907-2914 and references cited therein.
3. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Olah, G. A.; Bucsí, I.; Aniszfeld, R.; Prakash, G. K. S. Carbon 1992, 30, 1203-1211. Hirsch, A. The Chemistry of the Fullerenes; Georg Thieme Verlag, Stuttgart, 1994. See also Boyd, P. D. W.; Bhyrappa, P.; Paul, P.; Stinchcombe, J.; Bolskar, R. D.; Sun, Y.; Reed, C. A. J. Am. Chem. Soc. 1995, 117, 2907-2914 and references cited therein.
4. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Olah, G. A.; Bucsí, I.; Aniszfeld, R.; Prakash, G. K. S. Carbon 1992, 30, 1203-1211. Hirsch, A. The Chemistry of the Fullerenes; Georg Thieme Verlag, Stuttgart, 1994. See also Boyd, P. D. W.; Bhyrappa, P.; Paul, P.; Stinchcombe, J.; Bolskar, R. D.; Sun, Y.; Reed, C. A. J. Am. Chem. Soc. 1995, 117, 2907-2914 and references cited therein.
5. Wudl, F.; Hirsh, A.; Khemani, K. C.; Suzuki, T.; Allemand, P. -M.; Koch, A.; Eckert, H.; Srdanov, G.; Webb, H. M. In Fullerenes Synthesis, Properties, and Chemistry of Large Carbon Clusters; Hammond, G. S., Kuck, V. J., Eds.; ACS Symposium Series 48, American Chemical Society: Washington, DC, 1992, pp 161-175.
6. (a) Hirsch, A.; Soi, A.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 766-768.
7. (b) Hirsch, A.; Grösser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061-1067.
8. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699.
9. I have been estimated as 0.29: Charton, M. In Progress in Physical Organic Chemistry; Taft, R. W., Ed.; Wiley: New York, 1981, Vol. 13, pp 119-251.
10. 60 derivative was also reported as an independent work: Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. 1994, 106, 1427-1429.
11. 60 derivative was also reported as an independent work: Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. 1994, 106, 1427-1429.
12. For example: (a) An, Y.-Z.; Anderson, J. L.; Rubin, Y. J. Org. Chem. 1993, 58, 4799-4801 and references cited therein.
13. (b) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; King, R. C. J. Am. Chem. Soc. 1993, 115, 5829-5830.
14. (c) Komatsu, K.; Kagayama, A.; Murata, Y.; Sugita, N.; Kobayashi, K.; Nagase, S. Chem. Lett. 1993, 2163-2166.
15. A systematic study on redox behaviors of organofullerenes has been reported: Suzuki, T.; Maruyama, Y.; Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359-1363.
16. Stinchcombe, J.; Penicaud, A.; Bhyrappa, P.; Boyd, P. D. W.; Reed, C. A. J. Am. Chem. Soc. 1993, 115, 5212-5217.
17. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491.
18. 60 radical: Morishima, A.; Yoshida, M.; Iyoda, M. Abstract II for the 69th Annual Meeting of Chemical Society of Japan, p. 1348(1995).
19. There might be a tendency that semiempirical AM1 calculations tend to give relatively low values for the 1,4-adducts in general.
20. Scrivens, W. A.; Bedworth, P. V.; Tour, J. M. J. Am. Chem. Soc. 1992, 114, 7917-7919.
21. Suffert, J. J. Org. Chem. 1989, 54, 509-510.
22. Numbering system used in the experimental section is according to the IUPAC system: Birkett, P. R.; Hitchcook, P. B.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Natire 1992, 357, 479-481.
23. This systematic name refers only to one of the racemic compounds, the other being 1-(1-octynyl)-11-(substituent)-1,11-dihydrofullerene-60.