[2 + 2] cycloreversion of [4.3.2]propella-1,3,11-trienes: An approach to cyclo[n]carbons from propellane-annelated dehydro[n]annulenes

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1762-1775

  Tobe, Yoshito ^a   Fujii, Toshihiko ^a   Matsumoto, Hideki ^a   Tsumuraya, Kunihiro ^a   Noguchi, Daisuke ^a   Nakagawa, Nobuko ^a   Sonoda, Motohiro ^a   Naemura, Koichiro ^a   Achiba, Yohji ^b   Wakabayashi, Tomonari ^c  

^a OSAKA UNIVERSITY   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INORGANIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOTOLYSIS; REACTION ANALYSIS; ULTRAVIOLET IRRADIATION;

EID: 0034008155     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993314z     Document Type: Article

References (80)

1. For reviews, see: (a) Weltner, W., Jr.; Van Zee, R. J. Chem. Rev. 1989, 89, 1713. (b) Maier, J. P. Chem. Soc. Rev. 1997, 21.
2. For reviews, see: (a) Weltner, W., Jr.; Van Zee, R. J. Chem. Rev. 1989, 89, 1713. (b) Maier, J. P. Chem. Soc. Rev. 1997, 21.
3. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
4. Kräschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
5. (a) Yang, S. H.; Pettiette, C. L.; Conceicao, J.; Cheshnovsky, O.; Smalley, R. E. Chem. Phys. Lett. 1987, 139, 233.
6. (b) Yang, S.; Taylor, K. J.; Craycraft, M. J.; Conceicao, J.; Pettiette, C. L.; Cheshnovsky, O.; Smalley, R. E. Chem. Phys. Lett. 1988, 144, 431.
7. (a) von Helden, G.; Hsu, M. T.; Gotts, N. G.; Kemper, P. R.; Bowers, M. T. Chem. Phys. Lett. 1993, 204, 13.
8. (b) Hunter, J.; Fye, J.; Jarrold, M. F. J. Phys. Chem. 1993, 97, 3460.
9. (a) von Helden, G.; Hsu, M.-T.; Kemper, P. R.; Bowers, M. T. J. Chem. Phys. 1991, 95, 3835.
10. (b) Hunter, J. M.; Fye, J. L.; Jarrold, M. F. J. Chem. Phys. 1993, 99, 1785.
11. For reviews, see: (a) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (b) Diederich, F. Nature 1994, 369, 199. (c) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 443. (d) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43. (e) Tobe Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, 1999, in press.
12. For reviews, see: (a) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (b) Diederich, F. Nature 1994, 369, 199. (c) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 443. (d) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43. (e) Tobe Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, 1999, in press.
13. For reviews, see: (a) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (b) Diederich, F. Nature 1994, 369, 199. (c) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 443. (d) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43. (e) Tobe Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, 1999, in press.
14. For reviews, see: (a) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (b) Diederich, F. Nature 1994, 369, 199. (c) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 443. (d) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43. (e) Tobe Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, 1999, in press.
15. For reviews, see: (a) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (b) Diederich, F. Nature 1994, 369, 199. (c) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 443. (d) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43. (e) Tobe Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, 1999, in press.
16. For reviews, (a) Schwarz, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1412. (b) Goroff, N. S. Acc. Chem. Res. 1996, 29, 77.
17. For reviews, (a) Schwarz, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1412. (b) Goroff, N. S. Acc. Chem. Res. 1996, 29, 77.
18. (a) Hunter, J.; Fye, J.; Jarrold, M. F. Science 1993, 260, 784.
19. (b) von Helden, G.; Gotts, N. G.; Bowers, M. T. Nature 1993, 363, 60.
20. (c) von Helden, G.; Gotts, N. G.; Bowers, M. T. J. Am. Chem. Soc. 1993, 113, 4363.
21. (d) McElvany, S. W.; Ross, M. M.; Goroff, N. S.; Diederich, F. Science 1993, 259, 1394.
22. (e) Hunter, J. M.; Fye, J. L.; Roskamp, E. J.; Jarrold, M. F. J. Phys. Chem. 1994, 98, 1810.
23. Strout, D. L.; Scuseria, G. E. J. Chem. Phys. 1996, 100, 6492.
24. Hoffmann, R. Tetrahedron 1966, 22, 521.
25. For a review, see: Plattner, D. A.; Li, Y.; Houk, K. N. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; p 1.
26. Kerr, T. H.; Hibbins, R. E.; Miles, J. R.; Fossey, S. J.; Somerville, W. B.; Sarre, P. J. Mon. Not. R. Astron. Soc. 1996, 283, L105.
27. (a) Diederich, F.; Rubin, Y.; Knobler, C. B.; Whetten, R. L.; Schriver, K.; Houk, K. N.; Li, Y. Science 1989, 245, 1088.
28. (b) Diederich, F.; Rubin; Y.; Chapman, O. L.; Goroff, N. S. Helv. Chim. Acta 1994, 77, 1441.
29. Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966.
30. (a) Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607.
31. (b) Rubin, Y.; Kahr, M.; Knobler, C. B.; Diederich, F.; Wilkins, C. L. J. Am. Chem. Soc. 1991, 113, 495.
32. Adamson, G. A.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1996, 1335.
33. (a) Masamune, S.; Suda, M.; Ona, H.; Leichter, L. M. J. Chem. Soc., Chem. Commun. 1972, 1269.
34. (b) Maier, G.; Hoppe, B. Tetrahedron Lett. 1973, 861.
35. (c) Maier, G.; Reisenauer, H. P. Tetrahedron Lett. 1976, 3591.
36. For a review, Leigh, W. J. Chem. Rev. 1993, 93, 487.
37. Paquette, L. A.; Wingard, R. E., Jr.; Photis, J. M. J. Am. Chem. Soc. 1974, 96, 5801.
38. (a) Peet, N. P.; Cargill, R. L.; Bushey, D. F. J. Org. Chem. 1973, 38, 1218.
39. (b) Tobe, Y.; Hoshino, T.; Kawakami, Y.; Sakai, Y.; Kimura, K.; Odaira, Y. J. Org. Chem. 1978, 43, 4334.
40. (c) Kakiuchi, K.; Tsugaru. T.; Takeda, M.; Wakaki, I.; Tobe, Y.; Odaira, Y. J. Org. Chem. 1985, 50, 488.
41. For preliminary reports, see: (a) Tobe, Y.; Fujii, T.; Naemura, K. J. Org. Chem. 1994, 59, 1236. (b) Tobe, Y.; Fujii, T.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. J. Am. Chem. Soc. 1996, 118, 2758. (c) Tobe, Y.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1800.
42. For preliminary reports, see: (a) Tobe, Y.; Fujii, T.; Naemura, K. J. Org. Chem. 1994, 59, 1236. (b) Tobe, Y.; Fujii, T.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. J. Am. Chem. Soc. 1996, 118, 2758. (c) Tobe, Y.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1800.
43. For preliminary reports, see: (a) Tobe, Y.; Fujii, T.; Naemura, K. J. Org. Chem. 1994, 59, 1236. (b) Tobe, Y.; Fujii, T.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. J. Am. Chem. Soc. 1996, 118, 2758. (c) Tobe, Y.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1800.
44. Wakabayashi, T.; Kohno, M.; Achiba, Y.; Shiromaru, H.; Momose, T.; Shida, T.; Naemura, K.; Tobe, Y. J. Chem. Phys. 1997, 107, 4783.
45. For a review, see: Zimmerman, H. E. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, p 131.
46. Conley, R. T.; Nowark, B. E. J. Org. Chem. 1961, 26, 692.
47. Hraft, M. E.; Pankowski, J. Synlett 1994, 865.
48. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
49. Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051.
50. Villiears, J.; Perriot, P.; Normant, J. F. Synthesis 1975, 458.
51. Although the mechanism of the formation of 24 is not certain, the possibility that it was produced by the nucleophilic attack of the organolithium reagent to the once formed 17b was excluded, since diyne 17b was inert to butyllithium under the reaction conditions.
52. (a) Chodkiewicz, W.; Cadiot, P. Compt. Rend. 1955, 241, 1055.
53. (b) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; p 213.
54. Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943.
55. For a review, see: Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, p 521.
56. (a) Alberts, A. H. Recl. Trav. Chim. Pays-Bas 1989, 108, 242.
57. (b) Fritch, J. R.; Vollhardt, K. P. C. Organometallics 1982, 1, 590.
58. For tetra-tert-butylhexapentaene, see: (a) Hartzler, H. D. J. Am. Chem. Soc. 1971, 93, 4527. (b) Negi, T.; Kaneda, T.; Mizuno, H.; Toyota, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1974, 47, 2398.
59. For tetra-tert-butylhexapentaene, see: (a) Hartzler, H. D. J. Am. Chem. Soc. 1971, 93, 4527. (b) Negi, T.; Kaneda, T.; Mizuno, H.; Toyota, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1974, 47, 2398.
60. Behr, O. M.; Eglinton, G.; Galbraith, A. R.; Raphael, R. A. J. Chem. Soc. 1960, 3614.
61. (a) O'Krongly, D.; Denmeade, S. R.; Chiang, M. Y.; Breslow, R. J. Am. Chem. Soc. 1985, 107, 5544.
62. (b) Scott, L. T.; Cooney, M. J.; Otte, C.; Puls, C.; Haumann, T.; Boese, R.; Carrol, P. J.; Smith, A. B., III; de Meijere, A. J. Am. Chem. Soc. 1994, 116, 10275.
63. (a) Okamura, W. H.; Sondheimer, F. J. Am. Chem. Soc. 1967, 89, 5991.
64. (b) McQuilkin, R. M.; Garratt, P. J.; Sondheimer, F. J. Am. Chem. Soc. 1970, 92, 6682.
65. (c) Anthony, J.; Knobler, C. B.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 406.
66. (d) Zhou, Q.; Carrol, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294.
67. (e) Guo, L.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. J. Chem. Soc., Chem. Commun. 1994, 243.
68. (f) Haley, M. M.; Brand, S. C.; Pak, J. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 836.
69. (g) Nishinaga, T.; Kawamura, T.; Komatsu, K. J. Org. Chem. 1997, 62, 5354.
70. (h) Pak, J. J.; Weakley, T. J. R.; Haley, M. M. J. Am. Chem. Soc. 1999, 121, 8182.
71. For recent reviews, see: (a) Haley, M. M. Synlett 1998, 557. (b) Haley, M. M.; Pak, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 201, 82.
72. For recent reviews, see: (a) Haley, M. M. Synlett 1998, 557. (b) Haley, M. M.; Pak, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 201, 82.
73. (a) Rossi, A.; Carpita, A.; Quirici, M. G.; Gaudenzi, M. L. Tertrahedron 1982, 38, 631.
74. (b) Huyne, C.; Linstrumelle, G. Tertrahedron 1988, 44, 6337.
75. - revealed that its structure was different from that of the carbon cluster generated from graphite by the laser vaporization; see ref 23.
76. Li, Y.; Rubin, Y.; Diederich, F.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1618.
77. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1980, 102, 4544. See also: Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalistagi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226.
78. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1980, 102, 4544. See also: Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalistagi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226.
79. Snyder, H. R.; Kruse, C. W. J. Am. Chem. Soc. 1958, 80, 1942.
80. Kosolapoff, G. M. J. Am. Chem. Soc. 1947, 69, 1002.