Carbene-bridgehead olefin-carbene rearrangement: Formation of the tetracyclo[4.3.0.02,8.04,7]nonane Skeleton by carbene CH insertion

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7476-7484

  Ströter, Thomas ^a   Szeimies, Günter ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; DEHALOGENATION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0038813005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984114a     Document Type: Article

References (21)

1. Taken in part from Ströfer, T., Dissertation, Humboldt-Universität, Berlin, 1997.
2. Jones, M., Jr. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press, Inc.: Stamford, 1998; Vol. 2, pp 77-96.
3. Eaton, P. E.; Hoffmann, K.-L. J. Am. Chem. Soc. 1987, 109, 5285-5286. Eaton, P. E.; Appell, R. B. J. Am. Chem. Soc. 1990, 112, 4055- 4057. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321-1323. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981-4992. See also: Hrovat, D. A.; Borden, W. T. Mol. Phys. 1997, 91, 891-895.
4. Eaton, P. E.; Hoffmann, K.-L. J. Am. Chem. Soc. 1987, 109, 5285- 5286. Eaton, P. E.; Appell, R. B. J. Am. Chem. Soc. 1990, 112, 4055-4057. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321-1323. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981-4992. See also: Hrovat, D. A.; Borden, W. T. Mol. Phys. 1997, 91, 891-895.
5. Eaton, P. E.; Hoffmann, K.-L. J. Am. Chem. Soc. 1987, 109, 5285- 5286. Eaton, P. E.; Appell, R. B. J. Am. Chem. Soc. 1990, 112, 4055- 4057. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321-1323. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981-4992. See also: Hrovat, D. A.; Borden, W. T. Mol. Phys. 1997, 91, 891-895.
6. Eaton, P. E.; Hoffmann, K.-L. J. Am. Chem. Soc. 1987, 109, 5285- 5286. Eaton, P. E.; Appell, R. B. J. Am. Chem. Soc. 1990, 112, 4055- 4057. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321-1323. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981-4992. See also: Hrovat, D. A.; Borden, W. T. Mol. Phys. 1997, 91, 891-895.
7. Eaton, P. E.; Hoffmann, K.-L. J. Am. Chem. Soc. 1987, 109, 5285- 5286. Eaton, P. E.; Appell, R. B. J. Am. Chem. Soc. 1990, 112, 4055- 4057. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321-1323. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981-4992. See also: Hrovat, D. A.; Borden, W. T. Mol. Phys. 1997, 91, 891-895.
8. Bunz, U.; Herpich, W.; Podlech, J.; Polborn, K.; Pratzel, A.; Stephenson, D. S.; Szeimies, G. J. Am. Chem. Soc. 1994, 116, 7637-7641.
9. Belzner, J.; Gareiß, B.; Polborn, K.; Schmid, W.; Semmler, K.; Szeimies, G. Chem. Ber. 1989, 122, 1509-1529.
10. Ströter, Th.; Jarosch, O.; Szeimies, G. Eur. J. Chem. 1999, 5, 2046-2055.
11. Gaussian 94 (Revision D.3); Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
12. Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
13. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
14. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, 37, 785.
15. Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian Inc.: Pittsburgh, 1996; p 64 and references therein.
16. For a discussion of unrestricted DFT methods on molecules with biradical character in their singlet states, see: Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043 and references therein. See also: Hrovavat, D. A.; Duncan, J. A.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 169-175.
17. For a discussion of unrestricted DFT methods on molecules with biradical character in their singlet states, see: Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043 and references therein. See also: Hrovavat, D. A.; Duncan, J. A.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 169-175.
18. The sum of the van der Waals radii of chlorine and hydrogen is 2.95 A. See: Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
19. Wiberg, K. B.; Walker, F. H.; Pratt, W. E.; Michl, J. J. Am. Chem. Soc. 1983, 105, 3638-3641.
20. Morf, J.; Szeimies, G. Tetrahedron Lett. 1986, 5363-5366.
21. Fuchs, J.; Szeimies, G. Chem. Ber. 1992, 125, 2517-2522.