Single electron transfer Diels-Alder reaction of fullerene with Danishefsky's diene

Synlett

Volumn , Issue 7, 1999, Pages 1130-1132

  Mikami, Koichi ^a   Matsumoto, Shoji ^a   Okubo, Yasutaka ^a   Suenobu, Tomoyoshi ^b   Fukuzumi, Shunichi ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Danishefsky's diene; Diels Alder reaction; Fullerene; Single electron transfer

Indexed keywords

ALKADIENE; FULLERENE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONSTANTS AND COEFFICIENTS; ELECTRON TRANSPORT; HIGH TEMPERATURE PROCEDURES; PHOTOCHEMISTRY;

EID: 0032813743     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2776     Document Type: Article

References (42)

1. (a) Krätschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
2. (b) Krätschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Chem. Phys. Lett. 1990, 170, 167.
3. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
4. Reviews: (a) Wudl, F. Acc. Chem. Res. 1992, 25, 157.
5. (b) Miller, G. Chem. Ind. 1993, 226.
6. (c) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
7. (d) Hirsch, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 1138.
8. (e) Hirsch, A. The Chemistry of the Fullerenes Thieme, Stuttgart, 1994.
9. (f) Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243.
10. (g) 'Sliwa, W. Full. Sci. & Tech. 1995, 3, 243.
11. (h) Hirsch, A. Synthesis 1995, 895.
12. (i) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
13. (j) Rubin, Y. Top. Curr. Chem. 1999, 199, 67.
14. (k) Hirsh, A. Top. Curr. Chem. 1999, 199, 1.
15. Reviews; Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. Danishefsky, S. J. Chemtracts 1989, 273.
16. Reviews; Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. Danishefsky, S. J. Chemtracts 1989, 273.
17. Reviews; Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. Danishefsky, S. J. Chemtracts 1989, 273.
18. (a) An, Y. -Z.; Anderson, J. L.; Rubin, Y. J. Org. Chem. 1993, 58, 4799.
19. (b) An, Y. -Z.; Ellis, G. A.; Viado, A. L.; Rubin, Y. J. Org. Chem. 1995, 60, 6353.
20. (c) Wilson, S. R.; Lu, Q. Tetrahedron Lett. 1993, 34, 8043.
21. Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075; and references cited therein.
22. Reviews on the mechanism of the Diels-Alder reactions in general: Houk, K. N.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682; Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81; Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 537; Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc. 1996, 118, 8755; and references cited therein.
23. Reviews on the mechanism of the Diels-Alder reactions in general: Houk, K. N.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682; Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81; Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 537; Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc. 1996, 118, 8755; and references cited therein.
24. Reviews on the mechanism of the Diels-Alder reactions in general: Houk, K. N.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682; Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81; Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 537; Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc. 1996, 118, 8755; and references cited therein.
25. Reviews on the mechanism of the Diels-Alder reactions in general: Houk, K. N.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682; Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81; Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 537; Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc. 1996, 118, 8755; and references cited therein.
26. On the possibility of intervention of electron transfer in the following cycloadditions, see: (a) The Diels-Alder reactions of electron-deficient dienophiles with electron-rich dienes: Kiselev, V. D.; Miller, J. J. Am. Chem. Soc. 1975, 97, 4036. Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035. Sustmann, R.; Lucking, G.; Kopp, G.; Rese, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1713. Sustmann, R.; Korth, H.-G.; Nuchter, U.; Siagouri-Feulner, I.; Sicking, W. Chem. Ber. 1991, 124, 2811. Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1993, 115, 11600.
27. On the possibility of intervention of electron transfer in the following cycloadditions, see: (a) The Diels-Alder reactions of electron-deficient dienophiles with electron-rich dienes: Kiselev, V. D.; Miller, J. J. Am. Chem. Soc. 1975, 97, 4036. Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035. Sustmann, R.; Lucking, G.; Kopp, G.; Rese, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1713. Sustmann, R.; Korth, H.-G.; Nuchter, U.; Siagouri-Feulner, I.; Sicking, W. Chem. Ber. 1991, 124, 2811. Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1993, 115, 11600.
28. On the possibility of intervention of electron transfer in the following cycloadditions, see: (a) The Diels-Alder reactions of electron-deficient dienophiles with electron-rich dienes: Kiselev, V. D.; Miller, J. J. Am. Chem. Soc. 1975, 97, 4036. Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035. Sustmann, R.; Lucking, G.; Kopp, G.; Rese, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1713. Sustmann, R.; Korth, H.-G.; Nuchter, U.; Siagouri-Feulner, I.; Sicking, W. Chem. Ber. 1991, 124, 2811. Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1993, 115, 11600.
29. On the possibility of intervention of electron transfer in the following cycloadditions, see: (a) The Diels-Alder reactions of electron-deficient dienophiles with electron-rich dienes: Kiselev, V. D.; Miller, J. J. Am. Chem. Soc. 1975, 97, 4036. Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035. Sustmann, R.; Lucking, G.; Kopp, G.; Rese, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1713. Sustmann, R.; Korth, H.-G.; Nuchter, U.; Siagouri-Feulner, I.; Sicking, W. Chem. Ber. 1991, 124, 2811. Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1993, 115, 11600.
30. On the possibility of intervention of electron transfer in the following cycloadditions, see: (a) The Diels-Alder reactions of electron-deficient dienophiles with electron-rich dienes: Kiselev, V. D.; Miller, J. J. Am. Chem. Soc. 1975, 97, 4036. Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035. Sustmann, R.; Lucking, G.; Kopp, G.; Rese, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1713. Sustmann, R.; Korth, H.-G.; Nuchter, U.; Siagouri-Feulner, I.; Sicking, W. Chem. Ber. 1991, 124, 2811. Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1993, 115, 11600.
31. 60: Vassilikogiannakis, G.; Orfanpoulos, M. Tetrahedron Lett. 1997, 38, 4323.
32. (c) [3+2] Cycloaddition of dipolar trimethylenemethane with electron-deficient olefins: Yamago, S.; Ejiri, S.; Nakamura, E.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5344. Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990, Vol. 2, p. 147.
33. (c) [3+2] Cycloaddition of dipolar trimethylenemethane with electron-deficient olefins: Yamago, S.; Ejiri, S.; Nakamura, E.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5344. Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990, Vol. 2, p. 147.
34. Solid state fullerene Diels-Alder reaction with anthracenes: Mikami, K.; Matsumoto, S.; Tonoi, T.; Okubo, Y.; Suenobu, T.; Fukuzumi, S. Tetrahedron Lett. 1998, 39, 3733. However, the energetics for the photoinduced electron transfer in the solid state is significantly different from that in solution where the solvent plays an important role.
35. 60 with ketenc silyl acetals via single electron transfer mechanism. (a) Mikami, K.; Matsumoto, S. Synlett 1995, 229.
36. (b) Mikami, K.; Matsumoto, S.; Ishida, A.; Takamuku, S., Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 11134. Also see:
37. (c) Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753.
38. Danishefsky, S.; Yan, C.-F.; Singh, R. K.; Gammill, R. B.; McCurry, Jr. P. M.; Fritsch, N.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 7001.
39. 2 calcd 848.0837, found 848.0817.
40. Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277.
41. .+ with the full structural optimization indicates that the unpaired electron density is the largest on the terminal carbon where the C-C bond formation may occur.
42. The increased ratio of 3b at prolonged reaction time may be ascribed to the isomerization under photoirradiation.