Dynamics for reactions of ion pairs in aqueous solution: Reactivity of tosylate anion ion paired with the highly destabilized 1-(4-methylphenyl)-2,2,2- trifluoroethyl carbocation

Journal of Physical Organic Chemistry

Volumn 23, Issue 8, 2010, Pages 730-734

  Teshima, Minami ^a   Tsuji, Yutaka ^a   Richard, John P ^b  

^a KURUME NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b UNIVERSITY AT BUFFALO   (United States)

Author keywords

Carbocation; Dynamics; Ion pair; Solvolysis

Indexed keywords

4-METHYLPHENYL; AQUEOUS SOLUTIONS; CARBOCATION; CARBOCATIONS; ION PAIRS; NON-BRIDGING OXYGEN; SULFONATE ESTERS;

ESTERIFICATION; ESTERS; OXYGEN; RATE CONSTANTS; SOLVENTS;

IONS;

EID: 77955148835     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1642     Document Type: Article

References (31)

1. J. M. Harris, Prog. Phys. Org. Chem. 1974, 11, 89-173.
2. D. J. Raber, J.M. Harris, P. v. R. Schleyer, In: Ions and Ion Pairs in Organic Reactions, (Ed.: M. Szwarc), John Wiley & Son, New York, 1974. Vol.2.
3. Y. Tsuji, S. H. Kim, Y. Saeki, K.-I. Yatsugi, M. Fujio, Y. Tsuno, Tetrahed ron Lett. 1995, 36, 1465-1468.
4. A. D. Allen, M. Fujio, O. S. Tee, T. T. Tidwell, Y. Tsuji, Y. Tsuno, K.-I.Yatsugi, J. Am. Chem. Soc. 1995, 117, 8974-8981.
5. Y. Tsuji, T. Mori, M. M. Toteva, J. P. Richard, J. Phys. Org. Chem. 2003, 16, 484-490.
6. Y. Tsuji, T. Mori, J. P. Richard, T. L. Amyes, M. Fujio, Y. Tsuno, Org. Lett. 2001, 3, 1237-1240.
7. J. P. Richard, Y. Tsuji, J. Am. Chem. Soc. 2000, 122, 3963-3964.
8. T. L. Amyes, M. M. Toteva, J. P. Richard, In: Reactive Intermediate Chemistry (Ed.: R. A. Moss, M. S. Platz, M. J. Jr), John Wiley & Sons, Hoboken, NJ, 2004. p 41-68.
9. Tsuji, Y. M. M. Toteva, T. L. Amyes, J. P. Richard, Org. Lett. 2004, 6, 3633-3636.
10. J. P. Richard, T. L. Amyes, M. M. Toteva, Y. Tsuji, Adv. Phys. Org. Chem. 2004, 39, 1-26.
11. Y. Tsuji, J. P. Richard, Chem. Rec. 2005, 5, 94-106.
12. Y. Tsuji, J. P. Richard, J. Am. Chem. Soc. 2006, 128, 17139-17145.
13. A. D. Allen, C. Ambidge, C. Che, H. Michael, R. J. Muir, T. T. Tidwell, J. Am. Chem. Soc. 1983, 2343-2350.
14. T. T. Tidwell, Angew. Chem., Int. Ed. Engl. 1984, 23, 20-32.
15. J. P. Richard, J. Am. Chem. Soc. 1986, 108, 6819-6820.
16. J. P. Richard, J. Am. Chem. Soc. 1989, 111, 1455-1465.
17. J. P. Richard, T. L. Amyes, L. Bei, V. Stubblefield, J. Am. Chem. Soc. 1990, 112, 9513-9519.
18. R. Stewart, K. C. Teo, Can. J. Chem. 1980, 58, 2491-2496.
19. A. D. Allen, I. C. Ambidge, C. Che, H. Micheal, R. J. Muir, T. Tidwell, J. Am. Chem. Soc. 1983, 105, 2343-2350.
20. S. Oae, T. Kitao, Y. Kitaoka, Tetrahedron 1963, 19, 827-832.
21. A. D. Allen, M. P. Jansen, K. M. Koshy, N. N. Mangru, T. T. Tidwell, J. Am. Chem. Soc. 1982, 104, 207-211.
22. J. P. Richard, W. P. Jencks, J. Am. Chem. Soc. 1984, 106, 1373-1383.
23. J. M. Risley, R. L. V. Etten, J. Am. Chem. Soc. 1979, 101, 252-253.
24. T. L. Amyes, I. W. Stevens, J. P. Richard, J. Org. Chem. 1993, 58, 6057-6066.
25. J. P. Richard, T. L. Amyes, M. M. Toteva, Acc. Chem. Res. 2001, 34, 981-988.
26. J. P. Richard, Tetrahedron 1995, 51, 1535-1573.
27. W. P. Jencks, Chem. Soc. Rev. 1981, 10, 345-375.
28. J. P. Richard, M. E. Rothenberg, W. P. Jencks, J. Am. Chem. Soc. 1984, 106, 1361-1372.
29. J. P. Richard, W. P. Jencks, J. Am. Chem. Soc. 1982, 104, 4689-4691.
30. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334-338.
31. I. Lee, S. C. Dong, J. J. Hak, Tetrahedron 1994, 50, 7981-7986.