AlCl3-catalyzed tandem acetylation of hydroarylated [60]fullerenes

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3335-3338

  Kokubo, Ken ^a   Tochika, Shinya ^a   Kato, Mai ^a   Sol, Yui ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALUMINUM CHLORIDE; ALUMINUM DERIVATIVE; BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; CHLORIDE; FULLERENE C60; FULLERENE DERIVATIVE; KETONE;

ACETYLATION; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ACETYLATION; ALCOHOLS; ALUMINUM COMPOUNDS; BENZENE DERIVATIVES; BIPHENYL COMPOUNDS; CATALYSIS; CHLORIDES; CYCLIZATION; FULLERENES; KETONES;

EID: 49649119725     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801239y     Document Type: Article

References (19)

1. Hirsch, A.; Brettreich, M. Fullerenes; Wiley-VCH: Weinheim, 2005.
2. Olah, G. A.; Bucsi, I.; Lambert, C.; Aniszfeld, R.; Trivedi, N. J.; Sensharma, D. K.; Prakash, G. K. S. J. Am. Chem. Soc. 1991, 113, 9387.
3. Olah, G. A.; Bucsi, I.; Ha, D. S.; Aniszfeld, R.; Lee, C. S.; Prakash, G. K. S. Fullerene Sci. Technol. 1997, 5, 389.
4. Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 3513.
5. Tochika, S.; Kato, M.; Kuang, C.; Kokubo, K.; Oshima, T. Abstracts of the 31st Fullerene-Nanotubes General Symposium 2006, 62.
6. Nambo, M.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2007, 129, 8080.
7. 2 fullerene carbons, consisting with the 1,2-addition to the [6,6]-bond.
8. (a) Pasquarello, A.; Schluter, M.; Haddon, R. C. Science 1992, 257, 1660.
9. (b) Prato, M.; Suzuki, T.; Wudl, F.; Lucchini, V.; Maggini, M. J. Am. Chem. Soc. 1993, 115, 7876.
10. Ho, T.-L. Tandem Organic Reactions; John Wiley & Sons: New York, 1992.
11. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
12. Such a Lewis acid catalyzed 5-exo-trig cyclization of the phenyl group to carbonyl function has been reported for electron-deficient ketones such as 1-trifluoromethyl-3-phenylpropanone: Aubert, C.; Bégué, J.-P.; Bonnet-Delpon, D.; Mesureur, D. J. Chem. Soc., Perkin Trans. 1 1989, 395.
13. Siedschalag, C.; Luftman, H.; Wolff, C.; Mattay, J. Tetrahedron 1997, 53, 3587.
14. Tada, T.; Ishida, Y.; Saigo, K. Org. Lett. 2007, 9, 2083.
15. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York; Chapter 12, p 760.
16. Buckle, M. J. C.; Fleming, I.; Gil, S. Tetrahedron Lett. 1992, 33, 4479.
17. Niyazymbetov, M. E.; Evans, D. H.; Lerke, S. A.; Cahill, P. A.; Henderson, C. C. J. Phys. Chem. 1994, 98, 13093.
18. (a) Winstein, S.; Traylor, T. G.; Garner, C. S. J. Am. Chem. Soc. 1955, 77, 3741.
19. (b) Abraham, M. H.; Hill, J. A. J. Organomet. Chem. 1967, 7, 11.