Synthesis of a propargyl alcohol having a C60 cage, its transformation into C60 derivatives with polar functional groups, and the solubility measurements

Tetrahedron

Volumn 54, Issue 10, 1998, Pages 2049-2058

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

^a KYOTO UNIVERSITY   (Japan)

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

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; FULLERENE; LITHIUM; ORGANIC SOLVENT; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ANALYSIS; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; SOLUBILITY;

EID: 0032485476     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10415-X     Document Type: Article

References (29)

1. 1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994. Hirsch, A. Synthesis 1995, 895-913. An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
2. 1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994. Hirsch, A. Synthesis 1995, 895-913. An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
3. 1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994. Hirsch, A. Synthesis 1995, 895-913. An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
4. 1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994. Hirsch, A. Synthesis 1995, 895-913. An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
5. 1. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685-693. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994. Hirsch, A. Synthesis 1995, 895-913. An, Y.-Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353-6361 and references cited therein. Diederich, F.; Thilgen, C. Science 1996, 271, 317-323.
6. 2. (a) Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Bull. Chem. Soc. Jpn. 1996, 69, 2143-2151.
7. (b) Tokuyama, H.; Yamago, S.; Nakamura, E.; Shiraki, T.; Sugitura, Y. J. Am. Chem. Soc. 1993, 115, 7918-7919.
8. (c) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem. Int. Ed. Engl. 1994, 33, 2462-2465.
9. (d) Friedman, S. H.; DeCamp, D. L.; Sijbesma, R. P.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6506-6509.
10. (e) Friedman, S. H.; Wudl, F.; Rubin, Y.; Kenyon, G. L. In Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials; Kadish, K. M., Ruoff, R. S. Eds.; Proc. Electrochem. Soc., 1994, pp. 662-669.
11. 60 derivatives, see: (a) Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235-5238.
12. (b) Ros, T. D.; Prato, M. J. Org. Chem. 1996, 61, 9070-9072.
13. 60 derivatives, see: Lamparth, I.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1994, 1727-1728, and references cited therein.
14. 60 derivatives, see: Lamparth, I.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1994, 1727-1728, and references cited therein.
15. 60 derivatives, see: Lamparth, I.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1994, 1727-1728, and references cited therein.
16. 4. Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102. Murata, Y.; Motoyama, K.; Komatsu, K.; Wan, T. S. M. Tetrahedron 1996, 52, 5077-5090.
17. 4. Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101-6102. Murata, Y.; Motoyama, K.; Komatsu, K.; Wan, T. S. M. Tetrahedron 1996, 52, 5077-5090.
18. 5. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491. Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947. Andersen, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
19. 5. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491. Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947. Andersen, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
20. 5. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491. Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947. Andersen, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
21. 5. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491. Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947. Andersen, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
22. 5. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697-9699. Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. J. Org. Chem. 1995, 60, 1490-1491. Timmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J.-F.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925-4947. Andersen, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366-1368. Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371-11372.
23. 6. For th examples of esterification of fullerene-containing alcohols, see: (a) Yamago, S.; Tokuyama, H.; Nakamura, E. J. Org. Chem. 1993, 58, 4796-4798.
24. (b) An, Y.-Z.; Anderson, J. L.; Rubin, Y. J. Org. Chem. 1993, 58, 4799-4801.
25. 13C NMR could not be obtained.
26. 8. Diederich, F.; Jones, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2445.
27. 9. (a) Sivaraman, N.; Dhamodaran, R.; Kaliappan, I.; Srinivasan, T. G.; Vasudeva Rao, P. R.; Mathews, C. K. J. Org. Chem. 1992, 57, 6077-6079.
28. (b) Ruoff, R. S.; Tes, D. S.; Malhotra, R.; Lorents, D. C. J. Phys. Chem. 1993, 97, 3379-3383.
29. 10. Scrivens, W. A.; Bedworth, P. V.; Tour, J. M. J. Am. Chem. Soc. 1992, 114, 7917-7919.