Conformational analysis of (1R*,4S*,7S*)-7-[(R*)-1,2-butadienyl]-1-methyl- bicyclo[2.2.1]hept-2-ene and (1R*,4S*,7S*)-7-[(S*)-1,2-butadienyl]-1-methyl- bicyclo[2.2.1]hept-2-ene. Molecular modeling as a complement to NMR for stereochemical analysis

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4455-4459

  Duncan, James A ^a  

^a LEWIS AND CLARK COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343868260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951418w     Document Type: Article

References (6)

1. Duncan, J. A.; Hendricks, R. T.; Kwong, Katy S. J. Am. Chem. Soc. 1990, 112, 8433-8442.
2. NOE results, taken from ref 1, were obtained using NOE difference spectroscopy: Upon irradiation of the bridgehead methyl group, an NOE enhancement was clearly observed for one of the epimers of 1 but not observed over the noise level for the other epimer. Clearly, the fact that we had both epimers 1a and 1b available to us for direct comparison was critical in enabling us to make the necessary distinction between the two.
3. These results also confirm the stereochemistry for the 1 → 2 + 3 rearrangement to be 1a → 95% (E)-2 + (Z)-3 and 1b → 96% (Z)-2 + (E)- 3, as was originally suggested in ref 1.
4. Gaussian 92, Revision G.3, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1992.
5. Spartan, Version 3.1. Wavefunction, Inc. 18401 Von Karman, Suite 370, Irvine, CA 92715.
6. CAChe, Release 3.5. CAChe Scientific Inc., Beaverton, OR.