Synthesis of Prototypical Fullerene Cyclopropanes and Annulenes. Isomer Differentiation via NMR and UV Spectroscopy

Journal of the American Chemical Society

Volumn 117, Issue 20, 1995, Pages 5492-5502

  Smith, Amos B ^a   Strongin, Robert M ^a   Brard, Laurent ^a   Furst, George T ^a   Romanow, William J ^a   Owens, Kevin G ^b   Goldschmidt, Robert J ^b   King, Richard C ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CARBON; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; PHOTOLYSIS; ULTRAVIOLET SPECTROSCOPY;

ANNULENES; CYCLOPROPANES;

FULLERENES;

EID: 0029309154     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00125a009     Document Type: Article

References (70)

1. Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994.
2. Review of methanofullerenes: Diederich, F.; Isaacs, L.; Philp, D. Chem. Soc. Rev. 1994, 243.
3. Creegan, K. M.; Robbins, J. L.; Robbins, W. K.; Millar, J. M.; Sherwood, R. D.; Tindall, P. J.; Cox, D. M.; Smith, A. B., III; McCauley, J. P., Jr.; Jones, D. R.; Gallagher, R. T. J. Am. Chem. Soc. 1992, 114, 1103.
4. 2 [6,5] annulene [Neumann, D. A.; Fischer, J. E.; Copley, J. R. D.; Heiney, P. A.; Rush, J. J.; Strongin, R. M.; Brard, L.; Smith, A. B., III Science and Technology of Fullerene Materials; Bernier, P.; Ebbesen, T. W., Bethune, D. S., Metzger, R. M., Chiang, L. Y., Mintmire, J. W., Eds.; Mater. Res. Soc. Proc.: Pittsburgh, PA, 1995, in press].
5. Preliminary communication: Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; King, R. C. J. Am. Chem. Soc. 1993, 115, 5829.
6. Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta 1993, 76, 1231.
7. Isaacs, L.; Diederich, F. Helv. Chim. Acta 1993, 76, 2454.
8. Diederich, F.; Isaacs, L.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1994, 391.
9. Osterodt, J.; Nieger, M.; Windschief, P.-M.; Vogtle, I. Chem. Ber. 1993, 126, 2331.
10. Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Castoro, J. A.; Wilkins, C.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6510.
11. Prato, M.; Lucchini, V.; Maggini, M.; Stimpfl, E.; Scorrano, G.; Eiermann, M.; Suzuki, T.; Wudl, F. J. Am. Chem. Soc. 1993, 115, 8479.
12. HIV protease inhibitor: Friedman, S. H.; DeCamp, D. L.; Slijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6506.
13. Polymers: Shi, S.; Khemani, K. C.; Li, Q.; Wudl, F. J. Am. Chem. Soc. 1992, 114, 10656.
14. Dendrite: Wooley, K. L.; Hawker, C. J.; Fréchet, J. M.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836.
15. Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. J. Am. Chem. Soc. 1992, 114, 7301.
16. 70 have been described. (a) Osmylation: Hawkins, J. M.; Meyer, A.; Solow, M. A. J. Am. Chem. Soc. 1993, 115, 7499.
17. Addition of bromomalonate anion, affording a cyclopropyl diester: Bkingel, C. Chem. Ber. 1993, 126, 1957.
18. 1,3-Dipolar addition of acetonitrile oxide and 4-methoxybenzonitrile oxide: Meier, M. S.; Poplawska, M.; Compton, A. L.; Shaw, J. P.; Selegue, J. P.; Guarr, T. F. J. Am. Chem. Soc. 1994, 116, 7044.
19. Organometallic addition of RH: Hirsch, A.; Grösser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061.
20. 2 isomers: Henderson, C. C.; Rohlfing, C. M.; Gillen, K. T.; Cahill, P. A. Science 1994, 264, 397.
21. Photochemical addition of a disilirane, reportedly at the equatorial belt (i.e., bond iv): Akasaka, T.; Mitsuhida, E.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 2627.
22. Equilibrating iridium complexes: Balch, A. L.; Catalano, V. J.; Lee, O. W.; Olmstead, M. M.; Parkin, S. R. J. Am. Chem. Soc. 1991, 113, 8953. Balch, A. L.; Lee, J. W.; Olmstead, M. M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1356.
23. Additions of alkyl radicals: Keizer, P. N.; Morton, J. R.; Preston, K. F. J. Chem. Soc., Chem. Commun. 1992, 1259.
24. The prefix regio as originally introduced by Alfred Hassner refers “to the directional preference of bond formation,” not to different regions of a molecule as often currently used, see: Hassner, A. J. Org. Chem. 1968, 33, 2684.
25. Preliminary communications: Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt, R. C. J. Chem. Soc., Chem. Commun. 1994, 2187.
26. Hoke, S. H., II; Molstad, J.; Dilettato, D.; Jay, M. J.; Carlson, D.; Kahr, B.; Cooks, R. G. J. Org. Chem. 1992, 57, 5069.
27. Wood, J. M.; Kahr, B.; Hoke, S. H., II; Dejarme, L.; Cooks, R. G.; Ben-Amotz, D. J. Am. Chem. Soc. 1991, 113, 5907.
28. Kalsbeck, W. A.; Thorpe, H. H. J. Electroanal. Chem. 1991, 314, 363.
29. 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.
30. Taylor, R.; Langley, G. J.; Meidine, M. F.; Parsons, J. P.; Abdul-Sada, A. K.; Denis, T. J.; Hare, J. P.; Kroto, H. W.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1992, 667.
31. Tuinman, A. A.; Mukherjee, P.; Adcock, J. L.; Hettich, R. L.; Compton, R. N. J. Phys. Chem. 1992, 96, 7584.
32. Taylor, R.; Langley, G. J.; Brisdon, A. K.; Holloway, J. H.; Hope, E. G.; Kroto, H. W.; Walto, D. R. M. J. Chem. Soc., Chem. Commun. 1993, 875.
33. Wudl, F. Acc. Chem. Res. 1992, 25, 106.
34. Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F.; Almarsson, O. Science 1991, 254, 1186.
35. Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F. J. Am. Chem. Soc. 1992, 114, 7300.
36. Shi, S.; Li, Q.; Khemani, K. C.; Wudl, F. J. Am. Chem. Soc. 1992, 114, 10656.
37. Vasella, A.; Uhlmann, P.; Waldraff, C. A. A.; Diederich, F.; Thilgen, C. Angew. Chem., Int. Ed. Engl. 1992, 31, 1388.
38. Crane, J. D.; Hitchcock, P. B.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1992, 1764.
39. Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685.
40. Yannoni, C. S.; Bernier, P. P.; Bethune, D. S.; Meijer, G.; Salem, J. R. J. Am. Chem. Soc. 1991, 113, 3190.
41. Hawkins, J. M.; Meyer, A.; Lewis, T. A.; Loren, S.; Hollander, F. J. Science 1991, 252, 312.
42. Fagan, P. J.; Calabrese, J. C.; Malone, B. Science 1991, 252, 548.
43. Balch, A. L.; Catalano, V. J.; Lee, J. W.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 5455.
44. After completion of this manuscript, Wudl [Janssen, R. A. J.; Hummelen, J. C.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 544] reported the photochemical conversion of substituted annulenes via a postulated di-π-methane mechanism to the corresponding cyclopropane.
45. Paulissen, R.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1972, 1465.
46. Mende, U.; Raduchel, B.; Skuballa, W.; Vorbrüggen, H. Tetrahedron Lett. 1975, 633. Suda, M. Synth. Commun. 1981, 714.
47. 60(or derivatives) based solely on mass intensities; Owens, K. G.; King, R. C., Drexel University, unpublished results.
48. Taylor, R.; Parsons, J. P.; Avent, A. G.; Rannard, S. P.; Dennis, T. J.; Hare, J. P.; Kroto, H. W.; Walton, D. R. M. Nature 1991, 351, 277.
49. Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. Org. Syn. 1970, 50, 27.
50. Roth, G.; Adelmann, P. J. Phys. I, Fr. 1992, 2, 1541.
51. McKenzie, D. R.; Davis, C. A.; Cockayne, D. J. H.; Muller, D. A.; Vassallo, A. M. Nature 1992, 355, 622.
52. Scuseria, G. E. Chem. Phys. Lett. 1991, 180, 451.
53. Haddon, R. C. Science 1993, 261, 1545.
54. Weigert, F. J.; Roberts, J. D. J. Am. Chem. Soc. 1967, 89, 5962
55. Weigert, F. J.; Roberts, J. D. J. Am. Chem. Soc. 1972, 94, 6021.
56. Rol, N. C.; Clague, A. D. H. Org. Magn. Reson. 1981, 16, 187.
57. Stöcker, M. Org. Magn. Reson. 1982, 20, 175.
58. Arnz, R.W.M. Carneiro, J.; Klug, W.; Schmickler, H.; Vogel, E.; Breuckmann, R.; Klärner, F.-G. Angew. Chem., Int. Ed. Engl. 1991, 30, 683.
59. Bax, A.; Freeman, R.; Frankiel, T. A.; Levitt, M. H. J. Magn. Reson. 1981, 43, 478.
60. Johnson, R. D.; Meijer, G.; Salem, J. R.; Bethune, D. S. J. Am. Chem. Soc. 1991, 113, 3619.
61. Hawkins, J. M.; Loren, S.; Meyer, A.; Nunlist, R. J. Am. Chem. Soc. 1991, 113, 7770.
62. Dykins, J., University of Pennsylvania, unpublished results.
63. Vogel, E.; Roth, H. D. Angew. Chem. 1964, 76, 145; Vogel, E.; Klug, W.; Breuer, A. Org. Synth. 1974, 54, 11.
64. Sondheimer, F.; Shani, A. J. Am. Chem. Soc. 1964, 86, 3168. Vogel, E.; Biskup, M.; Pretzer, W.; Böll, W. A. Angew. Chem. 1964, 76, 785. Vogel, E.; Klug, W.; Breuer, A. Org. Synth. 1976, 55, 86.
65. Balch, A. L.; Costa, D. A.; Lee, J. W.; Noll, B. C.; Olmstead, M. M. Inorg. Chem. 1994, 33, 2071.
66. 2; see: Ishida, T.; Tanaka, K.; Furudate, T.; Nogami, T.; Kubota, M.; Kurono, S.; Ohashi, M. Fullerene Sci. Technol. 1995, 3, 85.
67. Hansen, P. E.; Poulsen, O. K.; Berg, A. Org. Magn. Reson. 1975, 7, 405.
68. de Boer, T. J.; Backer, H. J. Org. Syn., Coll. Vol. 4 1963, 250.
69. Krätschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
70. Scrivens, W. A.; Bedworth, P. V.; Tour, J. M. J. Am. Chem. Soc. 1992, 114, 7917.