Convenient syntheses of 6,5 open and 6,6 closed cycloalkylidenefullerenes

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4651-4654

  Li, Zizhong ^a   Bouhadir, Kamal H ^a   Shevlin, Philip B ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030200249     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00917-3     Document Type: Article

References (12)

1. 1. For reviews see: a) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
2. b) Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243.
3. c) Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
4. 2. An exception is the parent methanofullerene in which the 6,5 open isomer appears to be more stable: a) Diederich, F.; Isaacs, L.; Philp, D. J. Chem. Soc. Perkin Trans. 2 1994, 391.
5. b) Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. J. Amer. Chem. Soc. 1992, 114, 7301.
6. c) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt; R. J.; King, R. C. J. Amer. Chem. Soc. 1995, 117, 5492.
7. 3. a) An, Y. Z.; Rubin, Y.; Schaller, C.; McElvany, J. Org. Chem. 1954, 59, 2927.
8. b) Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1366.
9. c) González, R.; Hummelen, J. C.; Wudl, F. J. Org. Chem. 1995, 60, 2618.
10. 4. Tosylhydrazones were prepared from the corresponding ketones. cis-3,4-bis-(alkoxycarbonyl)-cyclopentanone: Gais, H. B.; Bulow, G.; Zatorski, A.; Jentsch, M.; Maidonis, P.; Hemmerle, H. J. Org. Chem. 1989, 54, 5115. trans-3,4-bis-(alkoxycarboyl)cyclopentanone: Rosenquist, A.; Kvarnstorm, I.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. Acta Chem. Scan. 1992, 46, 1127.
11. 4. Tosylhydrazones were prepared from the corresponding ketones. cis-3,4-bis-(alkoxycarbonyl)-cyclopentanone: Gais, H. B.; Bulow, G.; Zatorski, A.; Jentsch, M.; Maidonis, P.; Hemmerle, H. J. Org. Chem. 1989, 54, 5115. trans-3,4-bis-(alkoxycarboyl)cyclopentanone: Rosenquist, A.; Kvarnstorm, I.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. Acta Chem. Scan. 1992, 46, 1127.
12. 3c