Synthesis and characterization of the first C70O epoxides. Utilization of 3He NMR in analysis of fullerene derivatives

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1904-1905

  Smith III, Amos B ^a   Strongin, Robert M ^a   Brard, Laurent ^a   Furst, George T ^a   Atkins, Joshua H ^a   Romanow, William J ^a   Saunders, Martin ^b   Jiménez Vázquez, Hugo A ^b   Owens, Kevin G ^c   Goldschmidt, Robert J ^c  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b YALE UNIVERSITY   (United States)

^c DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001116465     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960104l     Document Type: Article

References (38)

1. Diederich, F.; Ettl, R.; Rubin, Y.; Whetten, R. L.; Beck, R.; Alvarez, M.; Anz, S.; Sehsharma, D.; Wudl, F.; Khemani, K. C.; Koch, A. Science 1991, 252, 548.
2. 70O oxidoannulene isomer would incorporate the bridging oxygen at the equatorial belt (i.e., single bond viii in Figure 1). Raghavachari, K.; Rohlfing, C. M. Chem. Phys. Lett. 1992, 197, 495.
3. Howard, J. B.; LaFleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadov, T. K. Carbon 1992, 30, 1183.
4. Heymann, D.; Chibante, L. P. F. Recl. Trav. Chim. Pays-Bas 1993, 112, 531.
5. Heymann, D.; Chibante, L. P. F. Chem. Phys. Lett. 1993, 207, 339.
6. Kreegan, K. M.; Robbins, J. L.; Robbins, W. K.; Millar, J. M.; Sherwood, R. D.; Tindall, P. J.; Cox, D. M.; McCauley, J. M., Jr.; Jones, D. R.; Gallagher, R.; Smith, A. B., III. J. Am. Chem. Soc. 1992, 114, 1103.
7. Smith, A. B., III; Strongin, R. M.; Brard, L.; Purst, G. T.; Romanow, W. J.; Owens, K. G.; King, R. C. J. Am. Chem. Soc. 1993, 115, 5829.
8. Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. Science 1991, 254, 1186.
9. Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt, R. J. J. Chem. Soc., Chem. Commun. 1994, 2187.
10. Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, K. G.; Langridge-Smith, P. R. R.; Millar, J. R. A.; Taylor, A. T. Tetrahedron Lett. 1995, 35, 9067.
11. Recently, this exception has been shown to be incorrect; see the following: Schick, G.; Grosser, T.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2289. Smith, A. B., III; Tokuyama, T. Tetrahedron 1996, in press
12. Recently, this exception has been shown to be incorrect; see the following: Schick, G.; Grosser, T.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2289. Smith, A. B., III; Tokuyama, T. Tetrahedron 1996, in press
13. (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
14. (b) Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta 1993, 76, 1231.
15. (c) Prato, M.; Lucchini, V.; Maggini, M.; Stimpfl, E.; Scorrano, G.; Eiermann, M., Suzuki, T.; Wudl, F. J. Am. Chem. Soc. 1993, 113, 8479.
16. (d) Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243.
17. (e) Hirsch. A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994.
18. Ishida, T.; Tanaka, K; Furudate, T.; Nogami, T.; Kubota, M.; Kurono, S.; Ohashi, M. Fullerene Sci. Technol. 1995, 3, 85.
19. Haddon, R. C. Science 1993, 261, 1545.
20. (a) Hawkins, J. M.; Meyer, A.; Solow, M. A. J. Am. Chem. Soc. 1993, 115, 7499.
21. (b) Bingel, C. Chem. Ber. 1993, 126, 1957.
22. (c) Meier, M. S.; Poplawska, M.; Compton, A. L.; Shaw, J. P.; Selegue, J. P.; Guarr, T. F. J. Am. Chem. Soc. 1994, 116, 7044.
23. (d) Hirsch, A.; Grösser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061.
24. (e) Henderson, C. C.; Rohlfing, C. M.; Gillen, K. T.; Cahill, P. A. Science 1994, 264, 397.
25. (f) Akasaka, T.; Mitsuhida, E.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116. 2627.
26. (g) Balch, A. L.; Catalano, V. J.; Lee, O. W.; Olmstead, M. M.; Parkin, S. R. J. Am. Chem. Soc. 1991, 113, 8953.
27. (h) Balch, A. L.; Lee, J. W.; Olmstead, M. M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1356.
28. (i) Keizer, P. N.; Morton, J. R.; Preston, K. F. J. Chem. Soc., Chem. Commun. 1992, 1259.
29. (j) Meidine, M. F.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.; Osamu, O.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Perkin Trans. 2 1994, 1189.
30. (k) Seiler, P.; Herrmann, A.; Diederich, F.; Thilgen, C.; ter Meer, H.-U.; Muller, W. H. Helv. Chim. Acta 1994, 77, 1689.
31. Balch, A. L.; Costa, D. A.; Lee, J. W.; Noll, B. C.; Olmstead, M. M. Inorg. Chem. 1994, 33, 2071.
32. Elemes, Y. Silverman, S. K.; Sheu, C.; Kao, M.; Foote, C. S.; Alvarez, M. M.; Whetten, R. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 351.
33. (a) Vogel, E.; Bishop, M.; Pretzer, W.; Boll, W. A. Angew Chem., Int. Ed. Engl. 1964, 3, 642.
34. (b) Sondheimer, F.; Shani, A. J. Am. Chem. Soc. 1964, 86, 3168.
35. Analysis in terms of integrated intensities was complicated by partial overlapping of numerous resonances in addition to the usual variations in relaxation times. We believe that the 3C peak and one 1C peak each represent two carbons.
36. (a) Saunders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Bangerter, B. W., Mroczkowski, S., Freedburg, D. I.; Anet, F. A. L. J. Am. Chem. Soc. 1994, 116, 3621.
37. (b) Saunders, M.; Jiménez-Vázquez, H. A.; Cross, R. J.; Billups, W. E.; Gesenberg, C.; McCord, D. Tetrahedron Lett. 1994, 35, 3869.
38. (c) Smith, A. B., III; Strongin, R. M.; Brard, L.; Romanow, W J.; Saunders, M.; Jiménez-Vázquez, H. A.; Cross, R. J. J. Am. Chem Soc. 1994, 116, 10831.