Novel cyclooctatetraene radical cation planarized by full annelation with bicyclo[2.1.1]hexene units

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4611-4613

  Nishinaga, Tohru ^a   Uto, Takayuki ^a   Komatsu, Koichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[2.1.1]HEXENE; CATION; CYCLOOCTATETRAENE; RADICAL; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CYCLIZATION; DERIVATIZATION; ELECTRON SPIN RESONANCE; OPTICAL ROTATION; SPECTRAL SENSITIVITY; THEORETICAL STUDY;

EID: 10044242586     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047930y     Document Type: Article

References (19)

1. Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives, and their Valence Isomers; CRC Press: Boca Raton, FL, 1987.
2. (a) Dessau, R. M. J. Am. Chem. Soc. 1970, 92, 6356.
3. (b) Shida, T.; Iwata, S. J. Am. Chem. Soc. 1973, 95, 3473.
4. (c) Bally, T.; Truttmann, L.; Dai, S.; Williams, F. J. Am. Chem. Soc. 1995, 117, 7916.
5. Gerson, F.; Felder, P.; Schmidlin, R.; Wong, H. N. C. J. Chem. Soc., Chem. Commun. 1994, 1659.
6. (a) Katz, T. J. J. Am. Chem. Soc. 1960, 82, 3784; 3785.
7. (b) Katz, T. J.; Strauss, H. L. J. Chem. Phys. 1960, 32, 1873.
8. (c) Strauss, H. L.; Katz, T. J.; Fraenkel, G. K. J. Am. Chem. Soc. 1963, 55, 2360.
9. Olah, G. A.; Staral, J. S.; Liang, G.; Paquette, L. A.; Melega, W. P.; Carmody, M. J. J. Am. Chem. Soc. 1977, 99, 3349.
10. Komatsu, K.; Nishinaga, T.; Aonuma, S.; Hirosawa, C.; Takeuchi, K.; Lindner, H. J.; Richter, J. Tetrahedron Lett. 1991, 32, 676. See also: Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012.
11. Komatsu, K.; Nishinaga, T.; Aonuma, S.; Hirosawa, C.; Takeuchi, K.; Lindner, H. J.; Richter, J. Tetrahedron Lett. 1991, 32, 676. See also: Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012.
12. (a) Gerson, F.; Lopez, J.; Akaba, R.; Nelsen, S. F. J. Am. Chem. Soc. 1981, 103, 6716.
13. (b) Clark, T.; Teasley, M. F.; Nelsen, S. F.; Wynberg, H. J. Am. Chem. Soc. 1987, 109, 5719.
14. Nishinaga, T.; Komatsu, K.; Sugita, N.; Lindner, H. J.; Richter, J. J. Am. Chem. Soc. 1993, 115, 11642.
15. Matsuura, A.; Komatsu, K. J. Am. Chem. Soc. 2001, 123, 1768.
16. Matsuura, A.; Nishinaga, T.; Komatsu, K. J. Am. Chem. Soc. 2000, 122, 10007.
17. 6Sb: C, 44.56; H, 3.74. Found: C, 40.52; H, 3.65. Because of the intrinsic instability of this salt under air, the repeated analysis did not give any better result.
18. Gaussian 98, revision A.5; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1998.
19. •+ is unfavorable because a part having double-bond character has to be placed in the endocyclic position.