[60]Fullerenoacetyl chloride as a versatile precursor for fullerene derivatives: Efficient ester formation with various alcohols

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2643-2645

  Ito, Hiroshi ^a   Tada, Tomoyuki ^a   Sudo, Masafumi ^a   Ishida, Yasuhiro ^a   Hino, Tetsuo ^b   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[60]FULLERENOACETYL CHLORIDE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; FULLERENE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; EXTRACTION; PRECURSOR; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141743464     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034793g     Document Type: Article

References (20)

1. Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 23, 243. Bingel C. Chem. Ber. 1993, 126, 1957.
2. Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 23, 243. Bingel C. Chem. Ber. 1993, 126, 1957.
3. (a) Wang, Y.; Cao, J.; Schuster, D. I.; Wilson, S. R. Tetrahedron Lett. 1995, 36, 6843.
4. (b) Hamada, M.; Hino, T.; Kinbara, K.; Saigo, K. Tetrahedron Lett. 2001, 42, 5069.
5. (a) Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F.; Almarsson, O. Science 1991, 254, 1186.
6. (b) Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta 1993, 76, 1231.
7. (c)Isaacs, L.; Diederich, F. Helv. Chim. Acta 1993, 76, 2454.
8. (d) Eiermann, M.; Wudl, F.; Prato, M.; Maggini, M. J. Am. Chem. Soc. 1994, 116, 8364.
9. For examples of in situ generation and subsequent reaction of methano[60]fullerenecarboxylic acid chlorides, see: (a) Woods, C. R.; Bourgeois, J.-P.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 3813. (b) Agrawal, Y. K. Fullerene Sci. Technol. 1997, 5, 275.
10. For examples of in situ generation and subsequent reaction of methano[60]fullerenecarboxylic acid chlorides, see: (a) Woods, C. R.; Bourgeois, J.-P.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 3813. (b) Agrawal, Y. K. Fullerene Sci. Technol. 1997, 5, 275.
11. 2/dioxane (1:1 v/v, 30 mL), and the soluble fraction was separated by filtration. The filtrate was evaporated to dryness to afford 1 as a brown solid (145 mg, 0.19 mmol, 72%).
12. 2 (20 mL), and the soluble fraction was separated by filtration. The filtrate was evaporated to dryness to afford 2 as a black solid (51 mg, 0.064 mmol, quant.).
13. In the MALDI-TOF-MS spectrum of 2, several unidentified peaks were observed. These peaks are probably due to the reaction of 2 with the matrix (dithranol) and/or the fragmentation of 2 caused by the laser irradiation. See the Supporting Information.
14. (a) Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
15. (b) Hassner, A.; Krepski, L. R.; Alexanian, V. Tetrahedron 1978, 34, 2069.
16. Lawson, G. E.; Kitaygorodskiy, A.; Sun, Y.-P. J. Org. Chem. 1999, 64, 5913.
17. 2 to afford the methyl ester as a brown solid (14.3 mg, 0.018 mmol, 96%).
18. For examples of [60]fullerene-biomolecule hybrids, see: (a) Murakami, H. ; Watanabe, Y.; Nakashima, N. J. Am. Chem. Soc. 1996, 118, 4484. (b) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed. 2000, 39, 4254. (c) Ishi-i, T.; Ono, Y.; Shinkai, S. Chem. Lett. 2000, 808.
19. For examples of [60]fullerene-biomolecule hybrids, see: (a) Murakami, H. ; Watanabe, Y.; Nakashima, N. J. Am. Chem. Soc. 1996, 118, 4484. (b) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed. 2000, 39, 4254. (c) Ishi-i, T.; Ono, Y.; Shinkai, S. Chem. Lett. 2000, 808.
20. For examples of [60]fullerene-biomolecule hybrids, see: (a) Murakami, H. ; Watanabe, Y.; Nakashima, N. J. Am. Chem. Soc. 1996, 118, 4484. (b) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed. 2000, 39, 4254. (c) Ishi-i, T.; Ono, Y.; Shinkai, S. Chem. Lett. 2000, 808.