Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents

Journal of Fluorine Chemistry

Volumn 131, Issue 12, 2010, Pages 1338-1343

  Paterová, Jana ^a   Skalický, Martin ^a   Rybáčková, Markéta ^a   Kvíčalová, Magdalena ^b   Cvačka, Josef ^c   Kvíčala, Jaroslav ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

^c INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

Cyclic sulfate; DFT; Fluoro Grignard reagent; Fluoroalcohol; Fluoroalkyl sulfate; Nucleophilic substitution; Perfluoroalkyl iodide; Perfluoroalkylmagnesium

Indexed keywords

EID: 78649630930     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2010.09.004     Document Type: Article

References (33)

1. G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, and B. McKusick 7th ed. Fluorine Compounds, Organic in Ullmann's Encyclopedia of Industrial Chemistry 2009 John Wiley & Sons Weinheim pp. 16-18 (el. ed.)
2. C. Wakselman 4th ed. B. Baasner, H. Hagemann, C. Tatlow, Houben-Weyl vol. E10b/1 1999 Georg Thieme Stuttgart 481 497
3. C. Tamborski A. Hudlický, Pavlath Chemistry of Organic Fluorine Compounds. II. A Critical Review 1995 ACS Washington 646 669
4. D.J. Burton, and P.A. Morken 4th ed. B. Baasner, H. Hagemann, C. Tatlow, Houben-Weyl vol. E10b/1 1999 Georg Thieme Stuttgart 465
5. C.F. Smith, E.J. Soloski, and C. Tamborski J. Fluorine Chem. 4 1974 35 45
6. D.J. Burton, and Z.Y. Yang Tetrahedron 48 1992 189 275
7. D.J. Burton, and L. Lu Top. Curr. Chem. 193 1997 45 89
8. S. Lavaire, R. Plantier-Royon, and C. Portella Tetrahedron Asym. 9 1998 213 226
9. J. Kvíčala, J.-C. Mouyrin, and O. Paleta J. Fluorine Chem. 113 2002 195 200
10. A.R. Katritzky, Z. Zhang, and M. Qi Tetrahedron Lett. 38 1997 7015 7018
11. G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, and B. McKusick Fluorine Compounds, Organic in Ullmann's Encyclopedia of Industrial Chemistry 7th ed. 2009 John Wiley & Sons Weinheim pp. 22-27 (el. ed.)
12. P.C. Griffiths, A.Y.F. Cheung, R.L. Jenkins, A.M. Howe, A.R. Pitt, R.K. Heenan, and S.M. King Langmuir 20 2004 1161 1167
13. T. Asakawa, M. Hashikawa, K. Amada, and S. Miyagishi Langmuir 11 1995 2376 2379
14. Y. G. Galyametdinov, W. Haase, L. Malykhina, A. Prosvirin, I. Bikchantaev, A. Rakhmatullin, K. Binnemans.Synthesis, mesomorphism, and unusual magnetic behaviour of lanthanide complexes with perfluoi mated counterions Chemistry - A European Journal 7(1),2001,pp:99-105.
15. O. Kysilka, M. Rybáčková, M. Skalický, M. Kvíčalová, J. Cvačka, and J. Kvíčala Collect. Czech. Chem. Commun. 73 2008 1799 1813
16. M. Skalický, M. Rybáčková, O. Kysilka, M. Kvíčalová, J. Cvačka, and J. Kvíčala J. Fluorine Chem. 130 2009 966 973
17. O. Kysilka, M. Rybáčková, M. Skalický, M. Kvíčalová, J. Cvačka, and J. Kvíčala J. Fluorine Chem. 130 2009 629 639
18. H.J. Reich, A.W. Sanders, A.T. Fiedler, and M.J. Bevan J. Am. Chem. Soc. 124 2002 13386 13387
19. N2-promoting solvent, HMPA, due to its high cancerogenity Br. J. Cancer 36 1977 564 571
20. C. Ni, J. Liu, L. Zhang, and J. Hu Angew. Chem. Int. Ed. 46 2007 786 789
21. N. Takechi, S. Ait-Mohand, M. Medebielle, and W.R. Dolbier Jr. Org. Lett. 4 2002 4671 4672
22. H. Blancou, S. Benefice, and A. Commeyras J. Fluorine Chem. 23 1983 57 66
23. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision D.01 2004 Gaussian, Inc. Wallingford, CT
24. A.A. Granovsky, Firefly version 7.1.G. http://www.classic.chem. msu.su/gran/firefly/index.html.
25. General Atomic and Molecular Electronic Structure System M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, and J.A. Montgomery J. Comput. Chem. 14 1993 1347 1363
26. P.Y. Ayala, and H.B. Schlegel J. Chem. Phys. 107 1997 375 384
27. B.H. Besler, K.M. Merz Jr., and P.A. Kollman J. Comput. Chem. 11 1990 431 439
28. U.C. Singh, and P.A. Kollman J. Comput. Chem. 5 1984 129 145
29. R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, and R. Gilliland GaussView, Version 3.09 2003 Semichem, Inc., Shawnee Mission, KS
30. C. Dapremont, P. Cals, A. Commeyras, and C. Amatore J. Fluorine Chem. 56 1992 249 258
31. Du Pont, GB 994607 (1965).
32. Chem. Abstr. 63 (1965) 11362c.
33. H. Liebig, and K. Ulm Chem.-Ztg. 99 1975 477 485