Nucleophilic substitution of chlorobis(4-methoxyphenyl)methane: Reactivity of carbenium ions in ILs-trifluoroethanol mixtures

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6675-6678

  Bini, Riccardo ^a   Chiappe, Cinzia ^a   Pieraccini, Daniela ^a   Piccioli, Paolo ^a   Pomelli, Christian Silvio ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Carbenium ions; Ionic liquids; SN1

Indexed keywords

CARBENOID; CHLOROBIS(4 METHOXYPHENYL)METHANE; METHANE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; IONIZATION; RACEMIC MIXTURE;

EID: 23944499545     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.143     Document Type: Article

References (36)

1. J.D. Holbrey, and K.R. Seddon Clean Prod. Proc. 1 1999 223 236
2. M.J. Earle, and K.R. Seddon Pure Appl. Chem. 72 2000 1391 1398
3. T. Welton Chem. Rev. 99 1999 2071 2083
4. P. Wasserscheid, and M. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
5. R. Sheldon Chem. Commun. 2001 2399 2407
6. H. Olivier-Bourbigou, and L. Magna J. Mol. Catal. A. 182 2002 419 437
7. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
8. J.S. Wilkes J. Mol. Catal. A 214 2004 11 17
9. P. Wasserscheid T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
10. T. Welton Coord. Chem Rew. 248 2004 2459 2477
11. C. Chiappe, and D. Pieraccini J. Phys. Org. Chem. 18 2005 275 297
12. J. Grodkowski, and P. Neta J. Phys. Chem. A 106 2002 11130 11134
13. N.L. Lancaster, P.A. Salter, T. Welton, and G.B. Young J. Org. Chem. 67 2002 8855 8861
14. N.L. Lancaster, and T. Welton J. Org. Chem. 69 2004 5986 5992
15. L. Crowhust, N.L. Lancaster, J.M.P. Arloandis, and T. Welton J. Am. Chem. Soc. 126 2004 11549 11555
16. A. Skrzypczac, and P. Neta Int. J. Chem. Kinet. 36 2004 253 258
17. N.L. Lancaster, P.A. Salter, T. Welton, and G.B. Young J. Org. Chem. 67 2002 8855 8861
18. C. Chiappe, D. Pieraccini, and P. Saullo J. Org. Chem. 68 2003 6710 6715
19. N.L. Lancaster, and T. Welton J. Org. Chem. 69 2004 5986 5992
20. L. Crowhurst, N.L. Lancaster, J.M. Perez Arlandis, and T. Welton J. Am. Chem. Soc. 126 2004 11549 11555
21. A. Skrzypczac, and P. Neta Int. J. Chem. Kinet. 36 2004 253
22. F. D'Anna, V. Frenna, R. Noto, V. Pace, and D. Spinelli J. Org. Chem. 70 2005 2828 2831
23. C. Wheeler, K.N. West, C.L. Liotta, and C.A. Eckert Chem. Commun. 2001 887 888
24. N.M.T. Lourenço, and C.A.M. Afonso Tetrahedron 2003 789 794
25. L. Brinchi, R. Germani, and G. Savelli Tetrahedron Lett. 44 2003 2027 2029
26. Z.M.A. Judeh, H.-Y. Shen, B.C. Chi, L.-C. Feng, and S. Selvatoshi Tetrahedron Lett. 43 2002 9381 9384
27. D.W. Kim, C.E. Song, and D.Y. Chi J. Org. Chem. 68 2003 4281 4285
28. K. Sasaki, S. Matsumura, and K. Toshima Tetrahedron Lett. 45 2004 7043 7047
29. The kinetic study of this process in acetonitrile/TFE has been performed by Mayr: H. Mayr, and S. Minegishi Angew. Chem., Int. Ed. 41 2002 4493
30. 3CN) for the kinetic investigations
31. 3CN/TFE mixture, which could be evidenced also by the progressive darkening of the solution.
32. R.W. Taft, J.L.M. Abboud, M.J. Kamlet, and M.H. Abraham J. Solut. Chem. 14 1985 153
33. M.J. Kamlet, J.L.M. Abboud, and R.W. Taft Prog. Phys. Org. Chem. 13 1981 485
34. K.K. Laali, and V.J. Gettwert J. Fluorine Chem. 107 2001 31 34
35. Frisch, M. J. et al. Gaussian 03. For the complete list of authors see www.gaussian.com.
36. 6]. The high viscosity of this salt prevents the application of the stopped-flow technique.