Influence of the structure of polyfluorinated alcohols on Brønsted acidity/hydrogen-bond donor ability and consequences on the promoter effect

Journal of Organic Chemistry

Volumn 76, Issue 4, 2011, Pages 1126-1133

  Vuluga, Daniela ^a   Legros, Julien ^a   Crousse, Benoit ^a   Slawin, Alexandra M Z ^b   Laurence, Christian ^c   Nicolet, Pierre ^c   Bonnet Delpon, Daniele ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

^c Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2-PROPANOL; ANTIPERIPLANAR; DIELS-ALDER REACTION; DONOR ABILITY; FLUORINATED ALCOHOL; FLUORINE ATOMS; H-BONDING; H-BONDS; OH GROUP; POSITIVE CORRELATIONS; PROMOTER EFFECT; SOLVENT-SOLUTE INTERACTIONS; STERIC HINDRANCES; SULFIDE OXIDATION; TRIFLUOROETHANOL;

CHEMICAL REACTIONS; ETHANOL; FLUORINE; RATE CONSTANTS; X RAY DIFFRACTION;

PROPANOL;

ALCOHOL; BRONSTED ACID; HEXAFLUORO 2 PROPANOL; TRIFLUOROETHANOL;

ACIDITY; ARTICLE; CHEMICAL STRUCTURE; FLUORINATION; HYDROGEN BOND; X RAY DIFFRACTION;

ACIDS; ALCOHOLS; HYDROGEN BONDING; MOLECULAR CONFORMATION; PROPANOLS; PROTONS; SOLVENTS; TRIFLUOROETHANOL; X-RAY DIFFRACTION;

EID: 79951594820     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023816     Document Type: Article

References (96)

1. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, 2008.
2. Uneyama, K. Organofluorine Chemistry; Blackwell Publishing: Oxford, 2006. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley: Weinheim, 2004.
3. Hiyama, T. Organofluorine Compounds, Chemistry and Applications; Springer: Berlin, 2000.
4. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry, Principles and Commercial Applications; Plenum: New York, 1994.
5. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358
6. Eberson, L.; Hartshorn, M. P.; Persson, O.; Radner, F. Chem. Commun. 1996, 2105-2112
7. Eberson, L.; Hartshorn, M. P.; Persson, O. J. Chem. Soc., Perkin Trans. 2 1995, 1735-1744
8. Laurence, C.; Nicolet, P.; Reichardt, C. Bull. Soc. Chim. Fr. 1987, 125-130
9. Laurence, C.; Gal, J. F. Lewis Basicity and Affinity Scales. Data and Measurement; Wiley: Chichester, 2010.
10. Othon, C. M.; Kwon, O. H.; Lin, M. M.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 12593-12598
11. Chatterjee, C.; Hovagimyan, G.; Gerig, J. T. In Current Fluoroorganic Chemistry; Soloshonok, V. A.; Mikami, K.; Yamazaki, T.; Welch, J. T.; Honek, J. F., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 2007; p 379.
12. Chatterjee, C.; Gerig, J. T. Biopolymers 2007, 87, 115-123
13. Roccatano, D.; Fioroni, M.; Zacharias, M.; Colombo, G. Protein Sci. 2005, 14, 2582-2589
14. Santiveri, C. M.; Pantoja-Uceda, D.; Rico, M.; Jimenez, M. A. Biopolymers 2005, 79, 150-162
15. Gerig, J. T. Biophys. J. 2004, 86, 3166-3175
16. Mulla, H. R.; Cammers-Goodwin, A. J. Am. Chem. Soc. 2000, 122, 738-739
17. Andersen, N. H.; Dyer, R. B.; Fesinmeyer, R. M.; Gai, F.; Liu, Z. H.; Neidigh, J. W.; Tong, H. J. Am. Chem. Soc. 1999, 121, 9879-9880
18. Hong, D.-P.; Hoshino, M.; Kuboi, R.; Goto, Y. J. Am. Chem. Soc. 1999, 121, 8427-8433
19. Cammers-Goodwin, A.; Allen, T. J.; Oslick, S. L.; McClure, K. F.; Lee, J. H.; Kemp, D. S. J. Am. Chem. Soc. 1996, 118, 3082-3090
20. For reviews on fluorinated alcohols, see: Shuklov, I. A.; Dubrovina, N. V.; Börner, A. Synthesis 2007, 2925-2943
21. Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29
22. Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004; pp 341-350.
23. For recent contributions on reactions in fluoroalcohol as solvents, see: Saito, A.; Kasai, J.; Konishi, T.; Hanzawa, Y. J. Org. Chem. 2010, 75, 6980-6982
24. Li, G.-X.; Qu, J. Chem. Commun. 2010, 2653-2655
25. Kirste, A.; Nieger, M.; Malkowsky, I. M.; Stecker, F.; Fischer, A.; Waldvogel, S. R. Chem.-Eur. J. 2009, 15, 2273-2277
26. Guérard, K. C.; Chapelle, C.; Giroux, M.-A.; Sabot, C.; Beaulieu, M.-A.; Achache, N.; Canesi, S. Org. Lett. 2009, 11, 4756-4759
27. De, K.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. J. Org. Chem. 2009, 74, 6260-6265
28. Willot, M.; Chen, J. C.; Zhu, J. Synlett 2009, 577-580
29. Philippe, C.; Milcent, T.; Crousse, B.; Bonnet-Delpon, D. Org. Biomol. Chem. 2009, 7, 2026-2028
30. Ratnikov, M. O.; Tumanov, V. V.; Smit, W. A. Angew. Chem., Int. Ed. 2008, 47, 9739-9742
31. Ilardi, E. A.; Stivala, C. A.; Zakarian, A. Org. Lett. 2008, 10, 1727-1730
32. Fustero, S.; Román, R.; Sanz-Cervera, J. F.; Simón-Fuentes, A.; Cuñat, A. C.; Villanova, S.; Murguía, M. J. Org. Chem. 2008, 73, 3523-3529
33. De, K.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Tetrahedron 2008, 64, 10497-10500
34. Westermaier, M.; Mayr, H. Chem.-Eur. J. 2008, 14, 1638-1647
35. Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2008, 73, 2894-2897
36. Heydari, A.; Khaksar, S.; Tajbakhsh, M. Synthesis 2008, 3126-3130
37. Berkessel, A.; Adrio, J. A.; Hüttenhain, D.; Neudörfl, J. M. J. Am. Chem. Soc. 2006, 128, 8421-8426
38. Sulfoxidation: Ravikumar, K. S.; Kesavan, V.; Bonnet-Delpon, D.; Bégué, J.-P. Org. Synth. 2003, vol. 80, 184-186
39. Ravikumar, K. S.; Bégué, J.-P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141-3144
40. Ravikumar, K. S.; Zhang, Y. M.; Bégué, J.-P.; Bonnet-Delpon, D. Eur. J. Org. Chem. 1998, 2937-2940
41. Epoxidation: Legros, J.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Eur. J. Org. Chem. 2002, 3290-3293
42. van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 248-250
43. ten Brink, G. J.; Fernandes, B. C. M.; van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. J. Chem. Soc., Perkin Trans. 1 2001, 224-228
44. Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863
45. van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. J. Chem. Soc., Perkin Trans. 1 2000, 377-380
46. van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Tetrahedron Lett. 1999, 40, 5239-5242
47. van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 263-264
48. Transformation of ketones into tetraoxanes and/or lactones: Žmitek, K.; Stavber, S.; Zupan, M.; Bonnet-Delpon, D.; Charneau, S.; Grellier, P.; Iskra, J. Bioorg. Med. Chem. 2006, 14, 7790-7795
49. Žmitek, K.; Stavber, S.; Zupan, M.; Bonnet-Delpon, D.; Iskra, J. Tetrahedron 2006, 62, 1479-1484
50. Berkessel, A.; Andreae, M. R. M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. 2002, 41, 4481-4484
51. Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295
52. ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433
53. Matsumoto, M.; Kobayashi, H. Heterocycles 1986, 24, 2443-2247
54. see also ref 9d.
55. Oxidative chlorination: Ben-Daniel, R.; de Visser, S. P.; Shaik, S.; Neumann, R. J. Am. Chem. Soc. 2003, 125, 12116-12117
56. Berkessel, A.; Adrio, J. A. J. Am. Chem. Soc. 2006, 128, 13412-13420
57. Berkessel, A.; Adrio, J. A. Adv. Synth. Catal. 2004, 346, 275-280
58. de Visser, S. P.; Kaneti, J.; Neumann, R.; Shaik, S. J. Org. Chem. 2003, 68, 2903-2912
59. For a convenient access to HFA patterns, see: Sridhar, M.; Narsaiah, C.; Ramanaiah, B. C.; Ankathi, V. M.; Pawar, R. B.; Asthana, S. N. Tetrahedron Lett. 2009, 50, 1777-1779
60. Kabat, M. M.; Garofalo, L. M.; Daniewski, A. R.; Hutchings, S. D.; Liu, W.; Okabe, M.; Radinov, R.; Zhou, Y. J. Org. Chem. 2001, 66, 6141-6150
61. Coulembier, O.; Sanders, D. P.; Nelson, A.; Hollenbeck, A. N.; Horn, H. W.; Rice, J. E.; Fujiwara, M.; Dubois, P.; Hedrick, J. L. Angew. Chem., Int. Ed. 2009, 48, 5170-5173
62. Filler, R.; Schure, R. M. J. Org. Chem. 1967, 32, 1217-1219
63. Stewart, R.; Van der Linden, R. Can. J. Chem. 1960, 38, 399-406
64. Chang, I. S.; Price, J. T.; Tomlinson, A. J.; Willis, C. J. Can. J. Chem. 1972, 50, 512-520
65. a's have been determined potentiometrically. See Supporting Information for details.
66. Taft, R. W.; Kamlet, M. J. J. Am. Chem. Soc. 1976, 98, 2886-2894
67. Reichardt, C. Angew. Chem, Int. Ed. Engl. 1965, 4, 29-40
68. Dimroth, K.; Reichardt, C. Justus Liebigs Ann. Chem. 1969, 727, 93-105
69. Dimroth, K.; Reichardt, C.; Siepmann, T.; Bohlmann, F. Liebigs Ann. Chem. 1963, 661, 1-37
70. Mayer, U.; Gutmann, V.; Gerger, W. Monatsh. Chem. 1975, 106, 1235-1257
71. Mayer, U.; Gerger, W.; Gutmann, V. Monatsh. Chem. 1977, 108, 489-498
72. Buncel, E.; Stairs, R. A.; Wilson, H. The Role of Solvent in Chemical Reaction; Oxford University Press: Oxford, 2003.
73. Reichardt, C. Solvents and Solvent Effect in Organic Chemistry, 3 rd ed.; Wiley: Weinheim, 2003.
74. Handbook of Solvents; Wypych, G., Ed.; ChemTec Publishing: Toronto, 2001.
75. Marcus, Y. The Properties of Solvents; Wiley: Chichester, 1998.
76. Sraidi, K. Ph.D. thesis, University of Nantes, 1991.
77. Catalan, J. J. Phys. Chem. B 2009, 113, 5951-5960
78. Riddle, F. L.; Fowkes, F. M. J. Am. Chem. Soc. 1990, 112, 3259-3264
79. 2 = 0.989). However, no rationale could be found to explain this observation.
80. Middleton, W. J.; Lindsey, R. V., Jr. J. Am. Chem. Soc. 1964, 86, 4948-4952
81. Berrien, J.-F.; Ourévitch, M.; Morgant, G.; Ghermani, N. E.; Crousse, B.; Bonnet-Delpon, D. J. Fluorine Chem. 2007, 128, 839-843
82. Kong, L.; Wang, J.; Fu, X.; Zhon, Y.; Meng, F.; Luo, T.; Liu, J. Carbon 2010, 48, 1262-1270
83. Snow, E. S.; Perkins, F. K.; Houser, E. J.; Badescu, S. C.; Reinecke, T. L. Science 2005, 307, 1942-1945 For a review, see: Grate, J. W. Chem. Rev. 2008, 108, 726-745
84. Vuluga, D.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Chem. Commun. 2008, 4954-4955
85. 2O = 5.35: Khalili, F.; Henni, A.; East, A. L. L. J. Chem. Eng. Data 2009, 54, 2914-2917
86. 3)CHOH with piperazine or any other amine assessed.
87. For a discussion on hydrogen-bonding/zwitterionic forms of α-trifluoromethyl-α′-aminoalcohols, see: Katagiri, T.; Fujiwara, Y.; Takahashi, S.; Uneyama, K. J. Fluorine Chem. 2005, 126, 1134-1139
88. Khaksar, S.; Heydari, A.; Tajbakhsh, M.; Bijanzadeh, H. R. J. Fluorine Chem. 2010, 131, 106-110
89. Reviews on the Povarov reaction: Bello, D.; Ramón, R.; Lavilla, R. Curr. Org. Chem. 2010, 14, 332-356
90. Kouznetsov, V. V. Tetrahedron 2009, 65, 2721-2750
91. Legros, J.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D. Synlett 2006, 1899-1902
92. Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219
93. Urry, W. H.; Nishihara, A; Niu, J. H. Y. J. Org. Chem. 1967, 32, 347-352
94. Legros, J.; Bolm, C. Chem.-Eur. J. 2005, 11, 1086-1092
95. Mesropyan, E. G.; Ambartsumyan, G. B.; Avetisyan, A. A.; Galstyan, A. S.; Arutyunova, I. R. Russ. J. Org. Chem. 2005, 41, 67-69
96. Sridharan, V.; Avendano, C.; Menéndez, J. C. Synthesis 2008, 1039-1044