Synthesis and properties of cationic π-conjugated systems stabilized by bicyclo[2.2.2]octene units

Synlett

Volumn , Issue 2, 2005, Pages 187-202

  Komatsu, Koichi ^a,b   Nishinaga, Tohru ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Aromatic stabilization; C C hyperconjugation; Cations; One electron oxidation; X ray crystallography

Indexed keywords

BICYCLO COMPOUND; BICYCLO[2.2.2]OCTENE; CATION; POLYCYCLIC AROMATIC COMPOUND; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CONJUGATION; CRYSTAL STRUCTURE; OXIDATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 13844289185     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837217     Document Type: Article

References (84)

1. (a) Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives, and their Valence Isomers; CRC Press: Boca Raton, 1987.
2. (b) Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, 2000.
3. Thematic Issue on Novel Aromatic Compounds; Tetrahedron 2001, 57, 3507-3808.
4. Thematic Issue on Aromaticity; Chem. Rev. 2001, 101, 1115-1566.
5. (e) Randic, M. Chem. Rev. 2003, 103, 3449.
6. (f) Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777.
7. (g) Kumaraswamy, S.; Jalisatgi, S. S.; Matzger, A. J.; Miljani, O.; Vollhardt, K. P. C. Angew. Chem. Int. Ed. 2004, 43, 3711; and the previous paper cited therein.
8. (a) Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; Wiley-VCH: Chichester, 1997.
9. (b) Electronic Materials: The Oligomer Approach; Mullen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998.
10. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
11. Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
12. (e) Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541.
13. (f) Nitzan, A.; Ratner, M. A. Science 2003, 300, 1384.
14. (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
15. (b) Johnson, C. R.; Tait, B. D.; Cieplak, A. S. J. Am. Chem. Soc. 1987, 109, 5875.
16. (a) For example of the X-ray structure of 1-adamantyl cation, see: Laube, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 349.
17. (b) For theoretical calculations of 2-methyl-2-butyl (t-pentyl) cation, see: Schleyer, P. V. R.; de Carneiro, J. W. M.; Koch, W.; Forsyth, D. A. J. Am. Chem. Soc. 1991, 113, 3990.
18. However, in the X-ray crystal structure of the salt of this cation, crystal-packing forces make the C-H hyperconjugation more favorable, see: Kato, T.; Reed, C. A. Angew. Chem. Int. Ed. 2004, 43, 2908.
19. (a) Gerson, F.; Lopez, J.; Akaba, R.; Nelsen, S. F. J. Am. Chem. Soc. 1981, 103, 6716.
20. (b) Nelsen, S.; Teasley, M. F.; Kapp, D. L.; Kessel, C. R.; Grezzo, L. A. J. Am. Chem. Soc. 1984, 106, 791.
21. Clark, T.; Teasley, M. F.; Nelsen, S. F.; Wynberg, H. J. Am. Chem. Soc. 1987, 109, 5719.
22. Komatsu, K.; Takeuchi, K.; Arima, M.; Waki, Y.; Shirai, S.; Okamoto, K. Bull. Chem. Soc. Jpn. 1982, 55, 3257.
23. Komatsu, K.; Akamatsu, H.; Okamoto, K. Tetrahedron Lett. 1987, 28, 5889.
24. (a) Komatsu, K.; Jinbu, Y.; Gillette, G. R.; West, R. Chem. Lett. 1988, 2029.
25. (b) Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195.
26. Matsuura, A.; Nishinaga, T.; Komatsu, K. J. Am. Chem. Soc. 2000, 122, 10007.
27. (a) Frank, N. L.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1995, 117, 2102.
28. (b) Bürgi, H.-B.; Baldridge, K. K.; Hardcastle, K.; Frank, N. L.; Gantzel, P.; Siegel, J. S.; Ziller, J. Angew. Chem., Int. Ed. Engl 1995, 34, 1454.
29. Matsuura, A.; Komatsu, K. J. Am. Chem. Soc. 2001, 123, 1768.
30. Matsuura, A.; Nishinaga, T.; Komatsu, K. Tetrahedron Lett. 1999, 40, 123.
31. Matsuura, A.; Nishinaga, T.; Komatsu, K. Tetrahedron Lett. 1997, 38, 3427.
32. Matsuura, A.; Nishinaga, T.; Komatsu, K. Tetrahedron Lett. 1997, 38, 4125.
33. Nishinaga, T.; Inoue, R.; Matsuura, A.; Komatsu, K. Org. Lett. 2002, 4, 1435.
34. Nishinaga, T.; Inoue, R.; Matsuura, A.; Komatsu, K. Org. Lett. 2002, 4, 4117.
35. Kochi, J. K.; Rathore, R.; Maguéres, P. L. J. Org. Chem. 2000, 65, 6826.
36. The similar structural change in bond length has been observed upon one-electron oxidation of adamantylidene-adamantane and sesquihomoadamantene: Rathore, R.; Lindeman, S. V.; Zhu, C.-J.; Schleyer, P. v. R.; Kochi, J. K. J. Org. Chem. 2002, 67, 5106.
37. Nishinaga, T.; Matsuura, A.; Komatsu, K. unpublished.
38. Aonuma, S.; Komatsu, K.; Takeuchi, K. Chem. Lett. 1989, 2107.
39. Komatsu, K.; Akamatsu, H.; Jinbu, Y.; Okamoto, K. J. Am. Chem. Soc. 1988, 110, 633.
40. (a) Komatsu, K.; Takahashi, K.; Okamoto, K. Tetrahedron Lett. 1979, 4747.
41. (b) Okamoto, K.; Takeuchi, K.; Komatsu, K.; Kubota, Y.; Ohara, R.; Arima, M.; Takahashi, K.; Waki, Y.; Shirai, S. Tetrahedron 1983, 39, 4011.
42. Oda, M.; Kainuma, H.; Miyatake, R.; Kuroda, S. Tetrahedron Lett. 2002, 43, 3485.
43. Komatsu, K.; Akamatsu, H.; Aonuma, S.; Jinbu, Y.; Maekawa, N.; Takeuchi, K. Tetrahedron 1991, 47, 6951.
44. Komatsu, K.; Nishinaga, T.; Maekawa, N.; Kagayama, A.; Takeuchi, K. J. Org. Chem. 1994, 59, 7316.
45. Kagayama, A.; Komatsu, K.; Nishinaga, T.; Takeuchi, K.; Kabuto, C. J. Org. Chem. 1994, 59, 4999.
46. (a) Lambert, J. B.; Zhao, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 400.
47. (b) Sekiguchi, A.; Matsuno, T.; Ichinohe, M. J. Am. Chem. Soc. 2000, 122, 11250.
48. Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825.
49. (a) Murthy, S.; Nagano, Y.; Beauchamp, J. L. J. Am. Chem. Soc. 1992, 114, 3573.
50. (b) Nagano, Y.; Murthy, S.; Beauchamp, J. L. J. Am. Chem. Soc. 1993, 115, 10805.
51. Jarek, R. L.; Shin, S. K. J. Am. Chem. Soc. 1997, 119, 6376.
52. Nishinaga, T.; Izukawa, Y.; Komatsu, K. J. Am. Chem. Soc. 2000, 122, 9312.
53. Nishinaga, T.; Izukawa, Y.; Komatsu, K. Tetrahedron 2001, 57, 3645.
54. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
55. Komatsu, K.; Nishinaga, T.; Aonuma, S.; Hirosawa, C.; Takeuchi, K.; Lindner, H. J.; Richter, J. Tetrahedron Lett. 1991, 32, 6767.
56. Nishinaga, T.; Komatsu, K.; Sugita, N. J. Chem. Soc., Chem. Commun. 1994, 2319.
57. Dewar, M. J. S.; Harget, A.; Haselbach, E. J. Am. Chem. Soc. 1969, 91, 7521.
58. Dessau, R. M. J. Am. Chem. Soc. 1970, 92, 6356.
59. Shida, T.; Iwata, S. J. Am. Chem. Soc. 1973, 95, 3473.
60. Nishinaga, T.; Komatsu, K.; Sugita, N.; Lindner, H. J.; Richter, J. J. Am. Chem. Soc. 1993, 115, 11642.
61. (a) Olah, G. A.; Staral, J. S.; Paquette, L. A. J. Am. Chem. Soc. 1976, 98, 1267.
62. (b) Olah, G. A.; Staral, J. S.; Liang, G.; Paquette, L. A.; Melega, W. P.; Carmody, M. J. J. Am. Chem. Soc. 1977, 99, 3349.
63. Wakamiya, A.; Nishinaga, T.; Komatsu, K. Chem. Commun. 2002, 1192.
64. Nakayama, J.; Kuroda, K. J. Am. Chem. Soc. 1993, 115, 4612.
65. Wakamiya, A.; Nishinaga, T.; Komatsu, K. J. Am. Chem. Soc. 2002, 124, 15038.
66. (a) Block, E.; Page, J.; Toscano, J. P.; Wang, C.; Zhang, X.; DeOrazio, R.; Guo, C.; Sheridan, R. S.; Towers, G. H. N. J. Am. Chem. Soc. 1996, 118, 4719.
67. (b) Viola, H.; Winkler, R. In Houben-Weyl, Methoden der Organische Chemie, Vol. E9a; Schaumann, E., Ed.; Thieme: Stuttgart, 1997, 209-249.
68. (a) Schroth, W.; Hintzsche, E.; Spitzner, R.; Imgartinger, H.; Siemund, V. Tetrahedron Lett. 1994, 35, 1973,
69. (b) Schroth, W.; Hintzsche, E.; Spitzner, R.; Ströhl, D.; Sieler, J. Tetrahedron 1995, 51, 13247.
70. Block, E.; Birringer, M.; DeOrazio, R.; Fabian, J.; Glass, R. S.; Guo, C.; He, C.; Lorance, E.; Qian, Q.; Schreder, T. B.; Shan, Z.; Thiruvazhi, M.; Wilson, G. S.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 5052.
71. For example, see: Capasso, S.; Zagari, A. Acta Crystallogr., Sect. B. 1981, 37, 1437.
72. Klar, G. In Houben-Weyl, Methoden der Organische Chemie, Vol. E9a; Schaumann, E., Ed.; Thieme: Stuttgart, 1997, 250-407.
73. Nishinaga, T.; Wakamiya, A.; Komatsu, K. Chem. Commun. 1999, 777.
74. Nishinaga, T.; Wakamiya, A.; Komatsu, K. Tetrahedron Lett. 1999, 40, 4375.
75. Sullivan, P. D. J. Am. Chem. Soc. 1968, 90, 3618.
76. For recent reviews, see: (a) Hotta, S. In Handbook of Organic Conductive Molecules and Polymers, Vol. 2; Nalwa, H. S., Ed.; Wiley: Chichester, 1997, Chap. 8.
77. (b) Bäuerle, P. In Electronic Materials: The Oligomeric Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 2.
78. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
79. Otsubo, T.; Aso, Y.; Takimiya, K. Bull. Chem. Soc. Jpn. 2001, 74, 1789.
80. (a) Brédas, J. L.; Street, G. B. Acc. Chem. Res. 1985, 18, 309.
81. (b) Heeger, A. J.; Kivelson, S.; Schrieffer, J. R.; Su, W.-P. Rev. Mod. Phys. 1988, 781, 60.
82. Wakamiya, A.; Yamazaki, D.; Nishinaga, T.; Kitagawa, T.; Komatsu, K. J. Org. Chem. 2003, 68, 8305.
83. Bäuerle, P. Adv. Mater. 1992, 4, 102.
84. Nishinaga, T.; Wakamiya, A.; Yamazaki, D.; Komatsu, K. J. Am. Chem. Soc. 2004, 126, 3163.