On 'pure axial' monosubstituted cyclohexanes: Cyclohexyl nitronate esters adopt O-equatorial conformations

Journal of the American Chemical Society

Volumn 121, Issue 50, 1999, Pages 11864-11870

  Davis, Matthew C ^a   Cornett, Ben ^a   Wu, Shaoxiong ^a   Snyder, James P ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; ESTER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONFORMATION; GEOMETRY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033596333     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993017u     Document Type: Article

References (36)

1. Hassel, O. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; Vol 6, pp 11-17. Barton, D. H. R. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; Vol 6, pp 1-10.
2. Hassel, O. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; Vol 6, pp 11-17. Barton, D. H. R. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; Vol 6, pp 1-10.
3. (a) Stereochemistry of Organic Compounds, Eliel, E. L.; Wilen, S. H., Eds.; John Wiley & Sons: New York, 1994; pp 1142-1163.
4. (b) Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995.
5. Bushweller, C. H. In Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995; pp 25-58.
6. Kang, F.; Lin, C. J. Am. Chem. Soc. 1997, 119, 8562-8563.
7. Cornett, B.; Davis, M.; Wu, S.; Nevins, N.; Snyder, J. J. Am. Chem. Soc. 1998, 120, 12146-12147.
8. (a) Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendnckson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129;
9. (b) http://www.schrodinger.com/macromodel2.html
10. Ref 4, footnote 13.
11. (a) 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 94, Gaussian, Inc.: Pittsburgh, PA, 1994. Becke, A. D. J. J. Chem. Phys. 1993, 98, 5648- 5652.
12. (a) 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 94, Gaussian, Inc.: Pittsburgh, PA, 1994. Becke, A. D. J. J. Chem. Phys. 1993, 98, 5648-5652.
13. (b) Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627. Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093-3100. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
14. (b) Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627. Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093-3100. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
15. (b) Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627. Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093-3100. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
16. Cambridge Crystallographic Data Centre: http://csdvx2.ccdc.cam.ac.uk/
17. Stereochemistry of Organic Compounds, Eliel, E. L.; Wilen, S. H., Eds.; John Wiley & Sons: New York, 1994; p 696.
18. Kang, F.; Yin, C; She, S. J. Org. Chem. 1996, 61, 5523-5527.
19. Kimura, J.; Kawashima, A.; Sugizaki, M.; Nemoto, N.; Mitsunobu, O. J. Chem. Soc., Chem. Commun. 1979, 303-304.
20. Mitsunobu, O.; Yoshida, N. Tetrahedron Lett. 1981, 22, 2295-2296.
21. Falck, J.; Yu, J. Tetrahedron Lett. 1992, 33, 6723-6726.
22. (a) Lemeiux, R. U.; Kullnig, R. K.; Bernstein, H. J.; Schneider, W. G. J. Am. Chem. Soc. 1958, 80, 6098-6105.
23. (b) Jensen, F. R.; Beck, B. H. J. Am. Chem. Soc. 1968, 90, 3251-3253.
24. (c) Anet, F. A. L.; Henrichs, P. M. Tetrahedron Lett. 1969, 741-744. (d) ref 1a, pp 712-713.
25. (a) Schneider, H.-J.; Hoppen, V. J. Org. Chem. 1978, 43, 3866-3873; (b) ref 2a, Table 11.15, p 717, 1994.
26. Anet, F. A. L. J. Am. Chem. Soc. 1962, 84, 1053-1054.
27. Gree, R.; Carrie, R. Bull. Soc. Chim. Fr. 1975, 1314-1318.
28. gNMR: Cherwell Scientific Publishing Limited; http://www. cherwell.com/ ProdHome.gnmrhome.html.
29. Equation 1 is derived by simple manipulation of previous expressions used to determine conformer populations by the J-value method: (a) Eliel, E. L. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; pp 5-7. (b) Terui, Y.; Tori, K. J. Chem. Soc., Perkin Trans. 2 1975, 127-133. (c) Abraham, R. J.; Medforth, C. J.; Smith, P. E. J. Comput.-Aided Mol. Design 1991, 5, 205-212.
30. Equation 1 is derived by simple manipulation of previous expressions used to determine conformer populations by the J-value method: (a) Eliel, E. L. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; pp 5-7. (b) Terui, Y.; Tori, K. J. Chem. Soc., Perkin Trans. 2 1975, 127-133. (c) Abraham, R. J.; Medforth, C. J.; Smith, P. E. J. Comput.-Aided Mol. Design 1991, 5, 205-212.
31. Equation 1 is derived by simple manipulation of previous expressions used to determine conformer populations by the J-value method: (a) Eliel, E. L. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1971; pp 5-7. (b) Terui, Y.; Tori, K. J. Chem. Soc., Perkin Trans. 2 1975, 127-133. (c) Abraham, R. J.; Medforth, C. J.; Smith, P. E. J. Comput.-Aided Mol. Design 1991, 5, 205-212.
32. Private communication from Dr. F. -A. Kang, Beijing Normal University.
33. Still, W.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
34. Barnes, T.; Hickinbottom, W. J. Chem. Soc. 1961, 953-956.
35. Winstein, S.; Holness, N. J. Am. Chem. Soc. 1955, 77, 5562-5578.
36. Perrin, D.; Armarego, W. Purification of Laboratory Chemicals; 3rd ed.; Pergamon Press: Elmsford, 1988.