Theoretical investigation of the stereoselective stepwise cope rearrangement of a 3-vinylmethylenecyclobutane

Journal of the American Chemical Society

Volumn 128, Issue 34, 2006, Pages 11106-11113

  Zhao, Yi Lei ^a,b   Suhrada, Christopher P ^a   Jung, Michael E ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC PROPERTIES; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

POTENTIAL ENERGY SURFACE; TRIALKYLSILOXY GROUPS; VINYLMETHYLENECYCLOBUTANES;

AROMATIC COMPOUNDS;

3 VINYLMETHYLENECYCLOBUTANE; CYCLOBUTANE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; COPE REARRANGEMENT; CYCLIZATION; DENSITY FUNCTIONAL THEORY; PHASE TRANSITION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SURFACE PROPERTY;

EID: 33748089379     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060913e     Document Type: Article

References (25)

1. Doering, W. v. E.; Cheng, X. H.; Lee, K.; Lin, Z. S. J. Am. Chem. Soc. 2002, 124, 11642.
2. Gajewski, J. J. Hydrocarbon Thermal Isomerizations. 2nd ed.: Elsevier Academic Press: Amsterdam, 2004.
3. Leber, P. A.; Baldwin, J. E. Acc. Chem. Res. 2002, 35, 279.
4. Suhrada, C. P.; Selçuki, C.; Nendel, M.; Cannizzaro, C.; Houk, K. N.; Rissing P.-J.; Baumann, D.; Hasselmann, D. Angew. Chem., Int. Ed. 2005, 44, 3548.
5. Dolbier, W. R.; Mancini, G. J. Tetrahedron Lett. 1975, 2141.
6. Kozhushkov, S. I.; Kuznetsova, T. S.; Zefirov, N. S. Dokl. Akad. Nauk SSSR 1988, 299, 1395.
7. Jung, M. E.; Nishimura, N.; Novack, A. R. J. Am. Chem. Soc. 2005, 127, 11206.
8. (a) Borden, W. T.; Loncharich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213.
9. (b) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
10. Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
11. Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67.
12. (e) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8378.
13. Hrovat, D. A.; Chen, J.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 2000, 122, 7456.
14. (a) Hrovat, D. A.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 1072.
15. (b) Weist, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
16. (c) Kozlowski, P. M.; Dupuis, M.; Davidson, E. R. J. Am. Chem. Soc. 1995, 117, 774.
17. (d) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 334.
18. (e) Staroverov, V. N.; Davidson, E. R. J. Am. Chem. Soc. 2000, 122, 186.
19. Frisch, M. J. et al. Gaussian 03, revision C.02.: Gaussian, Inc.: Wallingford, CT, 2004.
20. Frisch, M. J. et al. Gaussian 98, revision A.9.; Gaussian, Inc.: Pittsburgh, PA, 1998.
21. Andersson, K. et al. Molcas. version 5.0.; Lund University: Sweden. 2001.
22. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445.
23. For the sake of consistency and simplicity, we will use the atom numbering system introduced in Figure 1, rather than the standard IUPAC numbering for the reactant or product, throughout the Results and Discussion section.
24. Korth, H. G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483.
25. Dolbier, W. R.; Koroniak, H.; Houk, K. N.; Sheu, C. M. Acc. Chem. Res. 1996, 29, 471.