Concentrated salt effects on the rates of solvolyses involving carbocations as reaction intermediates in acetone-water mixed solvents

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 1998, Pages 1961-1965

  Manege, Ludovick C ^a,c   Ueda, Tadaharu ^a   Hojo, Masashi ^a   Fujio, Mizue ^b  

^a KOCHI UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003138464     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802786b     Document Type: Article

References (46)

1. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
2. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
3. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
4. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
5. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
6. J. E. Gordon, in The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975; Ions and Ion Pairs in Organic Reactions, ed. M. Szwarc, Wiley-Interscience, New York, 1972, vol. 1; 1974, vol. 2; Advances in Physical Organic Chemistry, ed. V. Gold and D. Bethell, Academic, London, 1977, vol. 14; A. Loupy and B. Tchoubar, in Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992; Organic Reaction Mechanisms 1994, ed. A. C. Knipe and W. E. Watts, Wiley, Chichester, 1994.
7. L. C. Manege, T. Ueda and M. Hojo, Bull. Chem. Soc. Jpn., 1988, 71, 589.
8. R. Snaith and D. S. Wright, in Lithium Chemistry, ed. A.-M. Sapse and P. v. R. Schleyer, Wiley, New York, 1995, ch. 8.
9. M. Hojo, H. Hasegawa and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1994, 1855; M. Hojo, H. Hasegawa, A. Mizobe, Y. Ohkawa and Y. Miimi, J. Phys. Chem., 1995, 99, 16 609; M. Hojo, H. Hasegawa and H. Yoneda, Bull. Chem. Soc. Jpn., 1996, 69, 971.
10. M. Hojo, H. Hasegawa and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1994, 1855; M. Hojo, H. Hasegawa, A. Mizobe, Y. Ohkawa and Y. Miimi, J. Phys. Chem., 1995, 99, 16 609; M. Hojo, H. Hasegawa and H. Yoneda, Bull. Chem. Soc. Jpn., 1996, 69, 971.
11. M. Hojo, H. Hasegawa and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1994, 1855; M. Hojo, H. Hasegawa, A. Mizobe, Y. Ohkawa and Y. Miimi, J. Phys. Chem., 1995, 99, 16 609; M. Hojo, H. Hasegawa and H. Yoneda, Bull. Chem. Soc. Jpn., 1996, 69, 971.
12. M. Hojo, T. Ueda, L. C. Manege and M. Yamasaki, 7th Kyushu International Symposium on Physical Organic Chemistry (KISPOC-VII), Fukuoka, Dec. 1997, Abstr. No. P12; M. Hojo, H. Hasegawa, H. Tsurui, K. Kawamura, S. Minami and A. Mizobe, Bull. Chem. Soc. Jpn., 1998, 71, 1619.
13. M. Hojo, T. Ueda, L. C. Manege and M. Yamasaki, 7th Kyushu International Symposium on Physical Organic Chemistry (KISPOC- VII), Fukuoka, Dec. 1997, Abstr. No. P12; M. Hojo, H. Hasegawa, H. Tsurui, K. Kawamura, S. Minami and A. Mizobe, Bull. Chem. Soc. Jpn., 1998, 71, 1619.
14. M. Hojo, T. Ueda, M. Nishimura, M. Matsui and S. Umetani, unpublished results.
15. M. Fujio, M. Goto, T. Yoshino, K. Funatsu, Y. Tsuji, S. Ouchi and Y. Tsuno, Mem. Fac. Sci. Kyushu Univ., Ser. C, 1987, 16, 85.
16. D. J. Raber, R. C. Bingham, J. M. Harris, J. L. Fry and P. v. R. Schleyer, J. Am. Chem. Soc., 1970, 92, 9577.
17. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 1956, 78, 2770.
18. M. Hojo, H. Nagai, M. Hagiwara and Y. Imai, Anal. Chem., 1987, 59, 1770.
19. E. H. Oelkers and H. C. Helgeson, Science, 1993, 261, 888.
20. T. W. Bentley and G. E. Carter, J. Am. Chem. Soc., 1982, 104, 5741.
21. J. L. Fry, C. J. Lancelot, L. K. M. Lam, J. M. Harris, R. C. Bingham, D. J. Raber, R. E. Hall and P. v. R. Schleyer, J. Am. Chem. Soc., 1970, 92, 2538.
22. T. W. Bentley and P. v. R. Schleyer, J. Am. Chem. Soc., 1976, 98, 7658.
23. S. Winstein, E. Clippinger, A. H. Fainberg and G. C. Robinson, J. Am. Chem. Soc., 1954, 76, 2597; S. Winstein, P. E. Klinedinst, Jr. and G. C. Robinson, J. Am. Chem. Soc., 1961, 83, 885.
24. S. Winstein, E. Clippinger, A. H. Fainberg and G. C. Robinson, J. Am. Chem. Soc., 1954, 76, 2597; S. Winstein, P. E. Klinedinst, Jr. and G. C. Robinson, J. Am. Chem. Soc., 1961, 83, 885.
25. M. Hojo, H. Hasegawa, Y. Miyauchi, H. Moriyama, H. Yoneda and S. Arisawa, Electrochim. Acta, 1994, 39, 629.
26. B. G. Cox and H. Maskill, J. Chem. Soc., Perkin Trans. 2, 1983, 1901.
27. P. A. H. Wyatt and Z. M. Zochowski, J. Chem. Res. (S), 1977, 252; M. J. Postle and P. A. H. Wyatt, J. Chem. Soc., Perkin Trans. 2, 1972, 474.
28. P. A. H. Wyatt and Z. M. Zochowski, J. Chem. Res. (S), 1977, 252; M. J. Postle and P. A. H. Wyatt, J. Chem. Soc., Perkin Trans. 2, 1972, 474.
29. M. Hojo and H. Hamada, unpublished results.
30. J. I. Brauman and W. C. Archie, Jr., J. Am. Chem. Soc., 1970, 92, 5981.
31. M. Oki, H. Ikeda and S. Toyota, Bull. Chem. Soc. Jpn., 1998, 71, 749.
32. M. Fujio, H. Morimoto, H.-J. Kim and Y. Tsuno, Bull. Chem. Soc. Jpn., 1997, 70, 1403; 3081.
33. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, 2nd edn., 1969.
34. T. W. Bentley, F. L. Schadt and P. v. R. Schleyer, J. Am. Chem. Soc., 1972, 94, 992.
35. S. Winstein, E. Grunwald and H. W. Jones, J. Am. Chem. Soc., 1951, 73, 2700.
36. S. Winstein, A. H. Fainberg and E. Grunwald, J. Am. Chem. Soc., 1957, 79, 4146.
37. R. M. Forbes and H. Maskill, J. Chem. Soc., Chem. Commun., 1991, 854; I. M. Gordon and H. Maskill, Chem. Soc. Rev., 1989, 18, 123; I. S. Koo, T. W. Bentley, D. H. Kang and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1991, 175.
38. R. M. Forbes and H. Maskill, J. Chem. Soc., Chem. Commun., 1991, 854; I. M. Gordon and H. Maskill, Chem. Soc. Rev., 1989, 18, 123; I. S. Koo, T. W. Bentley, D. H. Kang and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1991, 175.
39. R. M. Forbes and H. Maskill, J. Chem. Soc., Chem. Commun., 1991, 854; I. M. Gordon and H. Maskill, Chem. Soc. Rev., 1989, 18, 123; I. S. Koo, T. W. Bentley, D. H. Kang and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1991, 175.
40. O. Rogne, J. Chem. Soc., B, 1969, 663.
41. C. A. Bunton and L. Robinson, J. Am. Chem. Soc., 1968, 90, 5965.
42. C. G. Swain and C. B. Scott, J. Am. Chem. Soc., 1953, 75, 141.
43. I. Lee and S. C. Kim, J. Korean Chem. Soc., 1973, 17, 406, cf. W. J. Spillane, F. A. McHugh and P. O. Burke, J. Chem. Soc., Perkin Trans. 2, 1998, 13.
44. I. Lee and S. C. Kim, J. Korean Chem. Soc., 1973, 17, 406, cf. W. J. Spillane, F. A. McHugh and P. O. Burke, J. Chem. Soc., Perkin Trans. 2, 1998, 13.
45. L. Menninga and J. B. F. N. Engberts, J. Phys. Chem., 1973, 77, 1271.
46. M. L. Chabinyc, S. L. Craig, C. K. Regan and J. I. Brauman, Science, 1998, 279, 1882.