Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes [6]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6297-6298

  Armstrong, Alan ^a,c   Washington, Ilyas ^b   Houk, K N ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE;

CHEMICAL REACTION KINETICS; CHIRALITY; CONFORMATION; EPOXIDATION; FLUORINATION; GEOMETRY; LETTER; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0034608915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000237v     Document Type: Letter

References (29)

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20. Studies of performic acid, dioxirane, peroxynitrous acid, and oxiziridine epoxidations have shown that B3LYP/6-31G(d) calculations provide transition structure and energies in accord with available experimental data and QCI calculations; see: (a) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (b) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982. (c) Bach, D. R.; Glukhovtsev, N. M.; Gonzalez, C. J. Am. Chem. Soc. 1998, 120, 9902.
21. Studies of performic acid, dioxirane, peroxynitrous acid, and oxiziridine epoxidations have shown that B3LYP/6-31G(d) calculations provide transition structure and energies in accord with available experimental data and QCI calculations; see: (a) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (b) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982. (c) Bach, D. R.; Glukhovtsev, N. M.; Gonzalez, C. J. Am. Chem. Soc. 1998, 120, 9902.
22. Studies of performic acid, dioxirane, peroxynitrous acid, and oxiziridine epoxidations have shown that B3LYP/6-31G(d) calculations provide transition structure and energies in accord with available experimental data and QCI calculations; see: (a) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (b) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982. (c) Bach, D. R.; Glukhovtsev, N. M.; Gonzalez, C. J. Am. Chem. Soc. 1998, 120, 9902.
23. All calculations were performed with Gaussian 98 (Revision A.2), Frisch, M. J. et al. Gaussian, Inc.: Pittsburgh, PA, 1998.
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25. 20b we find that 2-fluoroethoxide has an anti preference of 1.9 kcal/mol (B3LYP/6- 31G(d)). Here the electrostatic repulsion overcomes hyperconjugation effects which favor the gauche conformation, (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994; p 609. (b) Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. J. Phys. Chem. 1995, 99, 9072.
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28. Armstrong, A.; Wailes, J. S.; Ahmed, G. A. Unpublished results.
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