Chemistry of fullerene epoxides: Synthesis, structure, and nucleophilic substitution-addition reactivity

Molecules

Volumn 17, Issue 6, 2012, Pages 6395-6414

  Tajima, Yusuke ^a,b   Takeshi, Kazumasa ^b   Shigemitsu, Yasuo ^c   Numata, Youhei ^d  

^a RIKEN   (Japan)

^b SAITAMA UNIVERSITY   (Japan)

^c FLOX Corporation   (Japan)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

Epoxidation; Fullerene; Lewis acid; Nucleophilic substitution; Regioselectivity

Indexed keywords

EPOXIDE; FULLERENE DERIVATIVE; LEWIS ACID;

CATALYSIS; CHEMISTRY; REVIEW; SYNTHESIS;

CATALYSIS; EPOXY COMPOUNDS; FULLERENES; LEWIS ACIDS;

EID: 84862984732     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17066415     Document Type: Review

References (44)

1. Beck, R. D.; Stoermer, C.; Schultz, C.; Michel, R.; Weis, P.; Brauchle, G.; Kappes, M. M. Enhanced coalescence upon laser desorption of fullerene oxides. J. Chem. Phys. 1994, 101, 3243-3250.
2. 2. Inorg. Chem. 1994, 33, 2071-2072.
3. 60 with dimethyldioxirane formation of an epoxide and a 1, 3-dioxolane derivative. Angew. Chem. Int. Ed. Engl. 1992, 31, 351-353.
4. 60 and single walled carbon nanotubes with methyltrioxorhenium-hydrogen peroxide. J. Mole. Catal. A Chem. 2006, 244, 267-270. (Pubitemid 43121422)
5. Hamano, T.; Mashino, T.; Hirobe, M. Oxidation of [60]fullerene by cytochrome p450 chemical models. J. Chem. Soc. Chem. Commun. 1995, 1537-1538.
6. 2. J. Am. Chem. Soc. 1995, 117, 8926-8932.
7. n (n = 2,..3). Int. J. Quantum Chem. 2000, 76, 23-43.
8. Curry, N. P.; Doust, B.; Jelski, D. A. Computational study of the combinatorial addition of oxygen to buckminsterfullerene J. Clust. Sci. 2000, 12, 385-390.
9. 3v symmetry. J. Org. Chem. 2002, 67, 1696-1698. (Pubitemid 34211620)
10. 60 oxides, Chem. Phys. Lett. 1998, 293, 302-308. (Pubitemid 128340800)
11. Shigemitsu, Y.; Kaneko, M.; Tajima, Y.; Takeuchi, K. Efficient acetalization of epoxy rings on a fullerene cage. Chem. Lett. 2004, 33, 1604.
12. The large-scale supply of fullerene epoxides was materialized by Frontier Carbon Corporation in Japan since 2007.
13. 60 with methyl-(trifluoromethyl) - dioxirane. J. Org. Chem. 1999, 64, 8363-8368.
14. Tajima, Y.; Osawa, S.; Takeuchi, K. Polyoxidized fullerene. RIKEN Rev. 1998, 17, 53-54.
15. 60 epoxidation and viable multiple oxide formation by theoretical study. J. Org. Chem. 2000, 65, 1093-1098. (Pubitemid 30117381)
16. Bach, R. D.; Wolber, G. J. Mechanism of oxygen transfer from oxaziridine to ethylene: The consequences of homo-homo interactions on frontier orbital narrowing. J. Am. Chem. Soc. 1984, 106, 1410-1415.
17. Bach, R. D.; Owensby, A. L.; Gonzalez, C.; Schlegel, B. W.; McDouall, J. J. Transition structure for the epoxidation of alkenes with peroxy acids. J. Am. Chem. Soc. 1991, 113, 2338-2339.
18. 84: Numbering, π-bond order calculations and addition pattern considerations. J. Chem. Soc. Perkin Trans. 1993, 2, 813-824.
19. 3COOHal affords an unusual 1, 3-dioxolano-[60]fullerene. Tetrahedron Lett. 2006, 47, 2969-2972.
20. + in solution. Tetrahedron Lett. 1993, 34, 7629-7632.
21. 60. J. Chem. Soc. Chem. Commun. 1995, 1071-1072.
22. Shigemitsu, Y.; Tajima, Y. Method for Manufacturing Fullerene Derivatives. U. S. Patent 7, 671, 219 B2, 2 March 2010.
23. Yang, X. B.; Huang, S. H.; Jia, Z. S.; Xiao, Z.; Jiang, Z. P.; Zhang, Q. Y.; Gan, L. B.; Zheng, B.; Yuan, G.; Zhang, S. W. Reactivity of fullerene epoxide: Preparation of fullerene-fused thiirane, tetrahydrothiazolidin-2-one, and 1, 3-dioxolane. J. Org. Chem. 2008, 73, 2513-2526.
24. Meskens, F. A. J. Methods for the preparation of acetals from alcohols or oxiranes and carbonyl compounds. Synthesis 1981, 1981, 501-522.
25. Lee, S. B.; Tanaka, T.; Endo, T. N-Benzyl pyridinium salts as new useful catalysts for transformation of epoxides to cyclic acetals, orthoesters, and orthocarbonates. Chem. Lett. 1990, 19, 2019-2022.
26. 3-catalysed reaction of epoxides with carbonyl compounds. Tetrahedron 1970, 26, 1311-1313.
27. Tajima, Y. RIKEN, Saitama, Japan, 2005, Unpublished data.
28. Tajima, Y.; Hara, T.; Honma, T.; Matsumoto, S.; Takeuchi, K. Lewis acid-assisted nucleophilic substitution of fullerene epoxide. Org. Lett. 2006, 8, 3203-3206.
29. Chen, Z. X.; Wang, G. W. One-pot sequential synthesis of acetoxylated [60]fullerene derivatives. J. Org. Chem. 2005, 70, 2380-2383.
30. 60 isomers. J. Phys. Chem. A 2000, 104, 3878-3883.
31. Bordwell, F. G. Are nucleophilic bimolecular concerted reactions involving four or more bonds a myth? Acc. Chem. Res. 1970, 3, 281-290.
32. 60 +. Science 2000, 289, 101-104. (Pubitemid 30463299)
33. +. J. Am. Chem. Soc. 2002, 124, 9360-9361. (Pubitemid 34856208)
34. 60:.. Direct observation of alkylfullerenyl cation intermediates. J. Am. Chem. Soc. 1999, 121, 4298-4299. (Pubitemid 29220314)
35. 2). J. Am. Chem. Soc. 2004, 126, 8874-8875.
36. 60 cation intermediates. Chem. Commun. 2002, 3062-3063. (Pubitemid 36044186)
37. Numata, Y.; Kawashima, J.; Hara, T.; Tajima, Y. One-pot synthesis of indolino[2', 3':1, 2][60]-fullerenes from fullerene epoxide: Lewis acid-assisted nucleophilic addition followed by intramolecular cyclization. Chem. Lett. 2008, 37, 1018-1019.
38. Chen, C. P.; Luo, C.; Ting, C.; Chuang S. C. Organic photovoltaics incorporating fulleroisoquinolinones as n-type materials. Chem. Commun. 2011, 47, 1845-1847.
39. 60 redox states by IR spectroscopy. Eur. J. Inorg. Chem. 2011, 1744-1749.
40. Zhu, B.; Wang, G. W. Synthesis of [60]fulleroindolines: Palladium-catalyzed heteroannulations of [60]fullerene with o-iodoanilines. J. Org. Chem. 2009, 74, 4426-4428.
41. Zhu, B.; Wang, G. W. Palladium-catalyzed heteroannulation of fullerene with anilides via C-H bond activation. Org. Lett. 2009, 11, 4334-4337.
42. Nambo, M.; Segawa, Y.; Itami, K. Aziridinofullerene: A versatile platform for functionalized fullerenes. J. Am. Chem. Soc. 2011, 133, 2402-2405.
43. Numata, Y.; Kawashima, J.; Tajima, Y. Substituent effect on reduction potentials of heterocyclicfused fullerene derivatives. ECS Trans. 2009, 16, 33-43.
44. Hammett, L. P. The effect of structure upon the reactions of organic compounds. benzene derivatives. J. Am. Chem. Soc. 1937, 59, 96-103.