Trimerization products of trifluoroacetone: Critical solvent effect on position and kinetics of anomeric equilibria

Journal of Organic Chemistry

Volumn 73, Issue 4, 2008, Pages 1209-1216

  Saaidi, Pierre Loïc ^a   Guyonnet, Mathieu ^a   Jeanneau, Erwann ^b   Fleurat Lessard, Paul ^a   Hasserodt, Jens ^a  

^a UNIVERSITÉ DE LYON   (France)

^b UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC EQUILIBRIA; TRIFLUOROACETONE; TRIMERIZATION;

POLYMERIZATION; REACTION KINETICS; SOLVENTS; X RAY ANALYSIS;

CARBOHYDRATES;

ACETONE; AMALGAM; CARBOHYDRATE DERIVATIVE; HYDROXYL GROUP; MAGNESIUM DERIVATIVE; PYRAN DERIVATIVE; SODIUM DERIVATIVE; SOLVENT; TRIFLUOROACETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; FLUORINATION; SOLVENT EFFECT; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 39349101056     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701669p     Document Type: Article

References (47)

1. Buschmann, H. J.; Fueldner, H. H.; Knoche, W. Ber. Bunsen-Ges. 1980, 84, 41-4.
2. Dhingra, M. M.; Tatta, K. R. Org. Magn. Reson. 1977, 9, 23-8.
3. Simmons, H. E., Jr.; Wiley, D. W. J. Am. Chem. Soc. 1960, 82, 2288-96.
4. Smith, F.; Stacey, M.; Tatlow, J. C. (National Research Development Corp.) GB 1957.
5. Jakubek, V.; Robertson, E. A., III; Abdourazak, A. H.; Markley, T. J.; Marsella, J. A.; Ober, C. K. Proc. SPIE Int. Soc. Opt. Eng. 2004, 5376, 554-564.
6. Henne, A. L.; Hinkamp, P. E. J. Am. Chem. Soc. 1954, 76, 5147-8.
7. Resconich, S. Ph.D. Thesis, Purdue University, 1961.
8. Dhingra, M. M.; Tatta, K. R. Org. Magn. Reson. 1975, 7, 189-90.
9. McBee, E. T.; Campbell, D. H.; Kennedy, R. J.; Roberts, C. W. J. Am. Chem. Soc. 1956, 78, 4597-8.
10. Fischer, R.; Gorls, H.; Nestler, B.; Poppitz, W. J. Prakt. Chem.-Chem. Zeit. 2000, 342, 72-74.
11. Miethchen, R. J. Fluorine Chem. 2004, 125, 895-901.
12. Begue, J. P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
13. Berkessel, A.; Adrio, J. A.; Huettenhain, D.; Neudorfl, J. M. J. Am. Chem. Soc. 2006, 128, 8421-8426.
14. Saaidi, P. L.; Jeanneau, E.; Bouchu, D.; Hasserodt, J. Polyhedron 2007, 26, 1191-1198.
15. Glacet, C. Bull. Soc. Chim. Fr. 1954, 21, 575-586.
16. Fang, X. M.; Gong, F. Y.; Ye, J. N.; Fang, Y. Z. Chromatographia 1997, 46, 137-140.
17. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11.
18. Reichardt, C. Solvents and Solvents Effects in Organic Chemistry; 2nd ed.; VCH: New York. 1990.
19. Marcus, Y. J. Solution Chem. 1984, 13, 599-624.
20. Kamlet, M. J.; Abboud, J. L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
21. Lakowicz, J. R. Principles of fluorescence spectroscopy, 2nd ed.; Kluwer Academic/Plenum: New York, 1999.
22. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470.
23. Lippert, E. Z. Naturforsch. a - Astrophys. Phys. Phys. Chem. 1955, 10, 541-545.
24. Webb, J. A.; Klijn, J. E.; Hill, P. A.; Bennett, J. L.; Goroff, N. S. J. Org. Chem. 2004, 69, 660-664.
25. Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Sprinter: New York, 1978.
26. Hong, D. P.; Hoshino, M.; Kuboi, R.; Goto, Y. J. Am. Chem. Soc. 1999, 121, 8427-8433.
27. Rajan, R.; Balaram, P. Int. J. Pept. Protein Res. 1996, 48, 328-336.
28. Berkessel, A.; Adrio, J. A. J. Am. Chem. Soc. 2006, 128, 13412-13420.
29. Taft, R. W.; Kamlet, M. J. J. Chem. Soc., Perkin Trans. 2 1979, 1723-1729.
30. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383.
31. Kamlet, M. J.; Abboud, J. L.; Taft, R. W. J. Am. Chem. Soc. 1977, 99, 6027-6038.
32. Kamlet, M. J.; Taft, R. W. J. Chem. Soc., Perkin Trans. 2 1979, 349-356.
33. Drago, R. S.; Vogel, G. C.; Needham, T. E. J. Am. Chem. Soc. 1971, 93, 6014-6026.
34. Drago, R. S.; Kroeger, M. K.; Stahlbush, J. R. Inorg. Chem. 1981, 20, 306-308.
35. Jeffrey, G. A. An Introduction to Hydrogen Bonding: Oxford University Press: New York, 1997.
36. Swain, C. G.; Swain, M. S.; Powell, A. L.; Alunni, S. J. Am. Chem. Soc. 1983, 105, 502-513.
37. Krygowski, T. M.; Fawcett, W. R. J. Am. Chem. Soc. 1975, 97, 2143-2148.
38. Muddasani, P. R.; Bozo, E.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1994, 77, 257-290.
39. Angyal, S. J.; Christofides, J. C. J. Chem. Soc., Perkin Trans. 2 1996, 1485-1491.
40. Molinaro, A.; De Castro, C.; Lanzetta, R.; Manzo, E.; Parrilli, M. J. Am. Chem. Soc. 2001, 123, 12605-12610.
41. Capon, B.; Walker, R. B. J. Chem. Soc., Perkin Trans. 2 1974, 1600-1610.
42. Brönsted, J. N.; Guggenheim, E. A. J. Am. Chem. Soc. 1927, 49, 2554-2584.
43. Grellepois, F.; Chorki, F.; Ourevitch, M.; Charneau, S.; Grellier, P.; McIntosh, K. A.; Charman, W. N.; Pradines, B.; Crousse, B.; Bonnet-Delpon, D.; Begue, J. P. J. Med. Chem. 2004, 47, 1423-1433.
44. Giuliano, J. J.; Hill, D. G. J. Am. Chem. Soc. 1946, 68, 2359-2362.
45. Silva, A. M.; da Silva, E. C.; da Silva, C. O. Carbohydr. Res. 2006, 341, 1029-1040.
46. Guthrie, J. P. Can. J. Chem. - Rev. Can. Chim. 1978, 56, 2342-2354.
47. Capon, B. Chem. Rev. 1969, 69, 407-498.