Computational investigation of the role of fluoride in Tamao oxidations

Chemistry - A European Journal

Volumn 8, Issue 21, 2002, Pages 5043-5048

  Mader, Mary M ^b,c   Norrby, Per Ola ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b GRINNELL COLLEGE   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Alcohols; Density functional calculations; Oxidation reaction mechanisms; Silicates

Indexed keywords

ALCOHOLS; COMPUTATIONAL METHODS; OXIDATION; PEROXIDES; PHASE EQUILIBRIA;

TRANSITION STATES;

FLUORINE COMPOUNDS;

ALCOHOL; FLUORIDE; SILANE; SILANE DERIVATIVE;

ANALYTIC METHOD; AQUEOUS SOLUTION; ARTICLE; BECKMANN REARRANGEMENT; CALCULATION; FLUORINATION; OXIDATION; PHASE TRANSITION; REACTION ANALYSIS; SEQUENCE ANALYSIS; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; OXIDATION REDUCTION REACTION;

CHEMISTRY, PHARMACEUTICAL; FLUORIDES; MODELS, MOLECULAR; OXIDATION-REDUCTION; SILANES;

EID: 2242455045     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021104)8:21<5043::AID-CHEM5043>3.0.CO;2-R     Document Type: Article

References (33)

1. a) K. Tamao, T Hayashi, Y. Ito in Frontiers of Organosilicon Chemistry (Eds.: A. R. Bassindale, P. P. Gaspar), Royal Society of Chemistry, Cambridge, 1991, pp. 197-207;
2. b) I. Fleming, Chemtracts: Org. Chem. 1996, 1-64;
3. c) G. R. Jones, L. Landais, Tetrahedron 1996, 52, 7599-7662.
4. K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics 1983, 2, 1694-1696.
5. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut, P. E. J. Sanderson, J. Chem. Soc. Perkin Trans. 1 1995, 317-336.
6. A. G. M. Barrett, J. Head, M. L. Smith, N. S. Stock, A. J. P. White, D. J. Williams, J. Org. Chem. 1999, 64, 6005-6018.
7. F. L. van Delft, M. de Kort, G. A. van der Marel, J. H. van Boom, Terrahedron: Asymmetry 1994, 5, 2261-2264.
8. a) T. W Lee, E. J. Corey, Org. Lett. 2001, 3, 3337-3339;
9. b) K. Itami, K. Mitsudo, J.-I. Yoshida, J. Org. Chem. 1999, 64, 8709-8714; J. A. Hunt, W. R. Roush, J. Org. Chem. 1997, 62, 1112-1124.
10. b) K. Itami, K. Mitsudo, J.-I. Yoshida, J. Org. Chem. 1999, 64, 8709-8714; J. A. Hunt, W. R. Roush, J. Org. Chem. 1997, 62, 1112-1124.
11. K. Tamao, Advances in Silicon Chemistry, Vol. 3, JAI, Greenwich, CT, 1996, pp. 1-62.
12. K. Tamao, N. Ishida, Y. Ito, M. Kumada, Org. Synth. 1990, 69, 96-105.
13. K. Tamao, A. Kawachi, Y. Tanaka, H. Ohtani, Y. Ito, Tetrahedron 1996, 52, 5765-5772.
14. K. Tamao, E. Nakajo, Y. Ito, J. Org. Chem. 1987, 52, 4414-4416.
15. J. D. Buynak, J. B. Strickland, G. W. Lamb, D. Khasnis, S. Modi, D. Williams, H. Zhang, J. Org. Chem. 1991, 56, 7076-7083.
16. T. J. Mickelson, J. L. Koviach, C. J. Forsyth, J. Org. Chem. 1996, 61, 9617-9620.
17. B. M. Trost, K. Imi, I. W. Davies, J. Am. Chem. Soc. 1995, 117, 5371-5372.
18. K. Tamao, N. Ishida, Tetrahedron Lett. 1984, 25, 4245-4248.
19. K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi, Y. Ito, J. Am. Chem. Soc. 1986, 108, 6090-6093.
20. M.M. Mader, P.-O. Norrby, J. Am. Chem. Soc. 2001, 123, 1970-1976.
21. SpartanSGI Version5.1.3, Wavefunction Inc., 18401 von Karman, Suite370. Irvine. CA92715.
22. a) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261;
23. b) P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222;
24. c) M. S. Gordon, Chem. Phys. Lett. 1980, 76, 163-168.
25. Jaguar 4.0, Schrodinger, Inc., Portland, Oregon, 2000.
26. B. Marten, K. Kim, C. Cortis, R, A. Friesner, R. B. Murphy, M. N. Ringnalda, D. Sitkoff, B. Honig, J. Phys. Chem. 1996, 10, 11775-11788,
27. R. Damrauer, L. W. Burggraf, L. P. Davis, M. S. Gordon, J. Am. Chem. Soc. 1988, 110, 6601-6606.
28. R. Damrauer, J. A. Hankin, Chem. Rev. 1995, 95, 1137-1160.
29. M. S. Gordon, L. P. Davis, L. W. Burggraf in Advances in Gas Phase Ion Chemistry, Vol. 1, JAI, Greenwich, CT, 1992, pp. 203-223.
30. H. Maskill. The Physical Basis of Organic Chemistry, Oxford University Press, Oxford, 1985.
31. R. R. Holmes, Chem. Rev. 1990, 90, 17-31.
32. A reviewer observes that a conceptually simpler explanation is that a diaxial relationship of the two most negatively charged ligands places them at a maximum distance from each other. The authors note that this argument complements that of optimal orbital overlap for diaxially positioned electronegative ligands.
33. R. Corriea, P. DeShong, J. Org. Chem. 2001, 66, 7159-7165.