Pyramidalized Olefins: A DFT Study of the Homosesquinorbornene and Sesquibicyclo[2.2.2]octene Nuclei

Journal of Organic Chemistry

Volumn 68, Issue 24, 2003, Pages 9186-9190

  Margtić, Davor ^a,c   Williams, Richard Vaughan ^b   Warrener, Ronald N ^c  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF IDAHO   (United States)

^c CENTRAL QUEENSLAND UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; PROBABILITY DENSITY FUNCTION;

BUTTERFLY BENDINGS; PYRAMIDALIZATION;

ORGANIC COMPOUNDS;

ALKENE DERIVATIVE; BICYCLO COMPOUND; HOMOSESQUINORBORNENE; SESQUIBICYCLO[2.2.2]OCTENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; COVALENT BOND; PREDICTION;

EID: 0344823742     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035110d     Document Type: Article

References (24)

1. Reviews: (a) Luef, W.; Keese, R. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1991; Vol. 20, p 231.
2. (b) Borden, W. T. Chem. Rev. 1989, 89, 1095.
3. For a summary of the pyramidalization found in the norbornenyl system, see refs 1 and 3.
4. Williams, R. V.; Colvin, M. E.; Tran, N.; Warrener, R. N.; Margetić, D. J. Org. Chem. 2000, 65, 562.
5. Williams, R. V.; Gadgil, V. R.; Garner, G. G.; Williams, J. D.; Vij, A. Tetrahedron Lett. 1999, 40, 2690.
6. Williams, R. V.; Edwards, W. D.; Gadgil, V. R.; Colvin, M. E.; Seidl, E. T.; van der Helm, D.; Hossain, M. B. J. Org. Chem. 1998, 63, 5268.
7. Marchand, A. P.; Alihodžić S.; Dong, E. Z.; Bott, S. G. Tetrahedron Lett. 1998, 39, 8055.
8. Menzek, A.; Krawiec, M.; Watson, W. H.; Balci, M. J. Org. Chem. 1991, 56, 6755.
9. Menzek, A.; Saraçoǧlu, N.; Krawiec, M.; Watson, W. H., Balci, M. J. Org. Chem. 1995, 60, 829.
10. Balci, M.; Bourne, S. A.; Menzek, A.; Saraçoǧlu, N.; Watson, W. H. J. Chem. Crystallogr. 1995, 25, 107.
11. Saraçoǧlu, N.; Menzek, A.; Sayan, S.; Salzner, U.; Balci, M. J. Org. Chem. 1999, 64, 6670.
12. Paquette, L. A.; Carr, R. V. C.; Charumilind, P.; Blount, J. F. J. Org. Chem. 1980, 45, 4922.
13. Nelsen, S. F.; Reinhardt, L. A. J. Phys. Org. Chem. 2001, 14, 847.
14. See, for example, refs 3-5 and 14-17 and references therein.
15. Warrener, R. N. Eur. J. Org. Chem. 2000, 3363.
16. Butler, D. N.; Margetić, D.; O'Neill, P. J. C.; Warrener, R. N. Synlett 2000, 1, 98.
17. Eckert-Maksić, M.; Margetić, D.; Rademacher, P.; Kowski, K. Tetrahedron Lett. 1993, 34, 6951-6954.
18. Eckert-Maksić, M.; Novak-Doumbouya, N.; Kiralj, R.; Kojić-Prodić, B. J. Chem Soc, Perkin Trans. 2 2000, 1483.
19. Antol, I.; Eckert-Maksić, M.; Margetić, D.; Maksić, Z. B.; Kowski, K.; Rademacher, P. Eur. J. Org. Chem. 1998, 1403, 3.
20. Margetić, D.; Warrener, R. N.; Butler, D. N. Ab Initio and DFT study of pyramidalisation in norbornene and norbornadiene-2,3-dicarboxylic anhydrides. In Sixth electronic computational chemistry conference (ECCC-6); Homeier. H., Ed.; Nov 1-30, 1999; paper 39, http://www.chemie.uni-regensburg.de/ECCC6/.
21. Camps, P.; Font-Bardia, M.; Méndez, N.; Pérez, F.; Pujol, X.; Solans, X.; Vázquez, S.; Vialta, M. Tetrahedron 1998, 54, 4679.
22. Gaussian 98, Revision A.5: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B. ; Scuseria, G. E.; Robb, M.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery Jr., J. A.; 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.
23. Margetić D.; Warrener, R. N.; Eckert-Maksić, M.; Antol, I. ; Glasovac, Z. Theor. Chem. Acc. 2003, 109, 182.
24. Can, H.; Zahn, D.; Balci, M.; Brickman, J. Eur. J. Org. Chem. 2003, 1111.