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Volumn 11, Issue 4, 1998, Pages 254-260

The Menschutkin reaction of benzyl p-toluenesulfonates with N,N-dimethylanilines. Evidence for the duality of SN1 and SN2 mechanisms

(6) Kim, Sung Hong a Yoh, Soo Dong b Lim, Chultack a Mishima, Masaaki a Fujio, Mizue a Tsuno, Yuho a

a KYUSHU UNIVERSITY (Japan)

b Kyungpook National University (South Korea)

Author keywords

Benzyl tosylates; Duality of SN1, SN2 mechanisms; Menschutkin reaction; Yukawa Tsuno equation

Indexed keywords

EID: 0007314995 PISSN: 08943230 EISSN: None Source Type: Journal
DOI: 10.1002/(sici)1099-1395(199804)11:4<254::aid-poc2>3.0.co;2-6 Document Type: Article

Times cited : (15)

References (46)

1
- 37049166378
- C. K. Ingold and E. Rothstein. J. Chem. Soc. 1217 (1928).
- (1928) J. Chem. Soc. , pp. 1217
- Ingold, C.K.¹ Rothstein, E.²

2
- 0002091013
- A. R. Katritzky and B. E. Brycki. Chem. Soc. Rev. 19, 83 (1990).
- (1990) Chem. Soc. Rev. , vol.19 , pp. 83
- Katritzky, A.R.¹ Brycki, B.E.²

3
- 0348162718
- D. J. McLennan. Acc. Chem. Res. 9, 281 (1976).
- (1976) Acc. Chem. Res. , vol.9 , pp. 281
- McLennan, D.J.¹

4
- 0003541233
- R. A. Sneen. Acc. Chem. Res. 6, 46 (1973).
- (1973) Acc. Chem. Res. , vol.6 , pp. 46
- Sneen, R.A.¹

5
- 0002541077
- J. M. Harris. Prog. Phys. Org. Chem. 11, 89 (1974).
- (1974) Prog. Phys. Org. Chem. , vol.11 , pp. 89
- Harris, J.M.¹

6
- 37049150616
- J. W. Baker and W. W. Nathan. J. Chem. Soc. 236 (1936).
- (1936) J. Chem. Soc. , pp. 236
- Baker, J.W.¹ Nathan, W.W.²

7
- 0000621060
- C. G. Swain and W. P. Langsdorf. J. Am. Chem. Soc. 73, 2813 (1951).
- (1951) J. Am. Chem. Soc. , vol.73 , pp. 2813
- Swain, C.G.¹ Langsdorf, W.P.²

8
- 0001676202
- F. P. Ballistreri, E. Maccarone and A. Mamo. J. Org. Chem. 41, 3364 (1976).
- (1976) J. Org. Chem. , vol.41 , pp. 3364
- Ballistreri, F.P.¹ Maccarone, E.² Mamo, A.³

9
- 0007256407
- T. Ando, H. Tanabe and H. Yamataka. J. Am. Chem. Soc. 106, 2084 (1984).
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 2084
- Ando, T.¹ Tanabe, H.² Yamataka, H.³

10
- 11744353539
- S.-D. Yoh, Y. Tsuno, M. Fujio, M. Sawada and Y. Yukawa. J. Chem. Soc., Perkin Trans. 27 (1989); S.-D. Yoh, PhD Thesis, Osaka University (1973).
- (1989) J. Chem. Soc., Perkin Trans. , pp. 27
- Yoh, S.-D.¹ Tsuno, Y.² Fujio, M.³ Sawada, M.⁴ Yukawa, Y.⁵

11
- 11744341169
- PhD Thesis, Osaka University
- S.-D. Yoh, Y. Tsuno, M. Fujio, M. Sawada and Y. Yukawa. J. Chem. Soc., Perkin Trans. 27 (1989); S.-D. Yoh, PhD Thesis, Osaka University (1973).
- (1973)
- Yoh, S.-D.¹

12
- 11744342721
- PhD Thesis, Kyungpook National University Taegu Korea
- S. H. Kim. PhD Thesis, Kyungpook National University Taegu Korea (1992); D.-Y. Cheong, S. H. Kim, M.-H. Lee, S.-D. Yoh, M. Fujio and Y. Tsuno. J. Korean Chem. Soc. 39, 643 (1995); S. H. Kim, S.-D. Yoh, M. Fujio, H. Imahori, M. Mishima and Y. Tsuno. Bull. Korean Chem. Soc. 16, 760 (1995).
- (1992)
- Kim, S.H.¹

13
- 0000775614
- S. H. Kim. PhD Thesis, Kyungpook National University Taegu Korea (1992); D.-Y. Cheong, S. H. Kim, M.-H. Lee, S.-D. Yoh, M. Fujio and Y. Tsuno. J. Korean Chem. Soc. 39, 643 (1995); S. H. Kim, S.-D. Yoh, M. Fujio, H. Imahori, M. Mishima and Y. Tsuno. Bull. Korean Chem. Soc. 16, 760 (1995).
- (1995) J. Korean Chem. Soc. , vol.39 , pp. 643
- Cheong, D.-Y.¹ Kim, S.H.² Lee, M.-H.³ Yoh, S.-D.⁴ Fujio, M.⁵ Tsuno, Y.⁶

14
- 21844490273
- S. H. Kim. PhD Thesis, Kyungpook National University Taegu Korea (1992); D.-Y. Cheong, S. H. Kim, M.-H. Lee, S.-D. Yoh, M. Fujio and Y. Tsuno. J. Korean Chem. Soc. 39, 643 (1995); S. H. Kim, S.-D. Yoh, M. Fujio, H. Imahori, M. Mishima and Y. Tsuno. Bull. Korean Chem. Soc. 16, 760 (1995).
- (1995) Bull. Korean Chem. Soc. , vol.16 , pp. 760
- Kim, S.H.¹ Yoh, S.-D.² Fujio, M.³ Imahori, H.⁴ Mishima, M.⁵ Tsuno, Y.⁶

15
- 0024994631
- M. Fujio, M. Goto, T. Susuki, I. Akasaka, M. Mishima and Y. Tsuno. Bull. Chem. Soc. Jpn. 63, 1146 (1990); M. Fujio, M. Goto, T. Susuki, M. Mishima and Y. Tsuno. J. Phys. Org. Chem. 3, 449 (1990); M. Fujio, I. Akasaka, S. H. Kim, M. Mishima, Y. Tsuji and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 18 131 (1991).
- (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 1146
- Fujio, M.¹ Goto, M.² Susuki, T.³ Akasaka, I.⁴ Mishima, M.⁵ Tsuno, Y.⁶

16
- 84986938763
- M. Fujio, M. Goto, T. Susuki, I. Akasaka, M. Mishima and Y. Tsuno. Bull. Chem. Soc. Jpn. 63, 1146 (1990); M. Fujio, M. Goto, T. Susuki, M. Mishima and Y. Tsuno. J. Phys. Org. Chem. 3, 449 (1990); M. Fujio, I. Akasaka, S. H. Kim, M. Mishima, Y. Tsuji and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 18 131 (1991).
- (1990) J. Phys. Org. Chem. , vol.3 , pp. 449
- Fujio, M.¹ Goto, M.² Susuki, T.³ Mishima, M.⁴ Tsuno, Y.⁵

17
- 0024994631
- M. Fujio, M. Goto, T. Susuki, I. Akasaka, M. Mishima and Y. Tsuno. Bull. Chem. Soc. Jpn. 63, 1146 (1990); M. Fujio, M. Goto, T. Susuki, M. Mishima and Y. Tsuno. J. Phys. Org. Chem. 3, 449 (1990); M. Fujio, I. Akasaka, S. H. Kim, M. Mishima, Y. Tsuji and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 18 131 (1991).
- (1991) Mem. Fac. Sci. Kyushu Univ., Ser. C , vol.18 , pp. 131
- Fujio, M.¹ Akasaka, I.² Kim, S.H.³ Mishima, M.⁴ Tsuji, Y.⁵ Tsuno, Y.⁶

18
- 33847797449
- F. L. Schadt, T. W. Bentley and P. v. R. Schleyer. J. Am. Chem. Soc. 98, 7667 (1976); T. W. Bentley, C. T. Bowen, D. H. Morten and P. v. R. Schleyer. J. Am. Chem. Soc. 103, 5466 (1981).
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 7667
- Schadt, F.L.¹ Bentley, T.W.² Schleyer, P.V.R.³

19
- 33845557174
- F. L. Schadt, T. W. Bentley and P. v. R. Schleyer. J. Am. Chem. Soc. 98, 7667 (1976); T. W. Bentley, C. T. Bowen, D. H. Morten and P. v. R. Schleyer. J. Am. Chem. Soc. 103, 5466 (1981).
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 5466
- Bentley, T.W.¹ Bowen, C.T.² Morten, D.H.³ Schleyer, P.V.R.⁴

20
- 37049151401
- E. Gelles, E. D. Hughes and C. K. Ingold. J. Chem. Soc. 2918 (1954).
- (1954) J. Chem. Soc. , pp. 2918
- Gelles, E.¹ Hughes, E.D.² Ingold, C.K.³

21
- 0346902263
- A. R. Katritzky, G. Musumarra, K. Sakizadeh, S. M. M. El-Shafie and B. Jovanovic. Tetrahedron Lett. 21, 2697 (1980); A. R. Katritzky, A. M. El-Mowafy, G. Musumarra, K. Sakizadeh, C. Sana-Ullah, S. M. M. El-Shafie and S. S. Thind. J. Org. Chem. 46, 3823 (1981); A. R. Katritzky, G. Musumarra and K. Sakizadeh. J. Org. Chem. 46, 3831 (1981); A. R. Katritzky and G. Musumarra. Chem. Soc. Rev. 13, 47 (1984).
- (1980) Tetrahedron Lett. , vol.21 , pp. 2697
- Katritzky, A.R.¹ Musumarra, G.² Sakizadeh, K.³ El-Shafie, S.M.M.⁴ Jovanovic, B.⁵

22
- 0345218804
- A. R. Katritzky, G. Musumarra, K. Sakizadeh, S. M. M. El-Shafie and B. Jovanovic. Tetrahedron Lett. 21, 2697 (1980); A. R. Katritzky, A. M. El-Mowafy, G. Musumarra, K. Sakizadeh, C. Sana-Ullah, S. M. M. El-Shafie and S. S. Thind. J. Org. Chem. 46, 3823 (1981); A. R. Katritzky, G. Musumarra and K. Sakizadeh. J. Org. Chem. 46, 3831 (1981); A. R. Katritzky and G. Musumarra. Chem. Soc. Rev. 13, 47 (1984).
- (1981) J. Org. Chem. , vol.46 , pp. 3823
- Katritzky, A.R.¹ El-Mowafy, A.M.² Musumarra, G.³ Sakizadeh, K.⁴ Sana-Ullah, C.⁵ El-Shafie, S.M.M.⁶ Thind, S.S.⁷

23
- 0344604714
- A. R. Katritzky, G. Musumarra, K. Sakizadeh, S. M. M. El-Shafie and B. Jovanovic. Tetrahedron Lett. 21, 2697 (1980); A. R. Katritzky, A. M. El-Mowafy, G. Musumarra, K. Sakizadeh, C. Sana-Ullah, S. M. M. El-Shafie and S. S. Thind. J. Org. Chem. 46, 3823 (1981); A. R. Katritzky, G. Musumarra and K. Sakizadeh. J. Org. Chem. 46, 3831 (1981); A. R. Katritzky and G. Musumarra. Chem. Soc. Rev. 13, 47 (1984).
- (1981) J. Org. Chem. , vol.46 , pp. 3831
- Katritzky, A.R.¹ Musumarra, G.² Sakizadeh, K.³

24
- 0001779463
- A. R. Katritzky, G. Musumarra, K. Sakizadeh, S. M. M. El-Shafie and B. Jovanovic. Tetrahedron Lett. 21, 2697 (1980); A. R. Katritzky, A. M. El-Mowafy, G. Musumarra, K. Sakizadeh, C. Sana-Ullah, S. M. M. El-Shafie and S. S. Thind. J. Org. Chem. 46, 3823 (1981); A. R. Katritzky, G. Musumarra and K. Sakizadeh. J. Org. Chem. 46, 3831 (1981); A. R. Katritzky and G. Musumarra. Chem. Soc. Rev. 13, 47 (1984).
- (1984) Chem. Soc. Rev. , vol.13 , pp. 47
- Katritzky, A.R.¹ Musumarra, G.²

25
- 0346291651
- A. Queen. Can. J. Chem. 57, 2646 (1979).
- (1979) Can. J. Chem. , vol.57 , pp. 2646
- Queen, A.¹

26
- 0031000754
- C. Lim, S. H. Kim, S.-D. Yoh, M. Fujio and Y. Tsuno. Tetrahedron Lett. 38, 3243 (1997).
- (1997) Tetrahedron Lett. , vol.38 , pp. 3243
- Lim, C.¹ Kim, S.H.² Yoh, S.-D.³ Fujio, M.⁴ Tsuno, Y.⁵

27
- 4043156699
- A. Ceccon, I. Papa and A. Fava. J. Am. Chem. Soc. 88, 4643 (1966).
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 4643
- Ceccon, A.¹ Papa, I.² Fava, A.³

28
- 37049062072
- P. Casapieri and E. R. Swart. J. Chem. Soc. 4342 (1961); 1254 (1963).
- (1961) J. Chem. Soc. , pp. 4342
- Casapieri, P.¹ Swart, E.R.²

29
- 11744347354
- P. Casapieri and E. R. Swart. J. Chem. Soc. 4342 (1961); 1254 (1963).
- (1963) J. Chem. Soc. , pp. 1254

30
- 0000116094
- edited by G. A. Olah and P. v. R. Schleyer, Chapt. 27, Wiley, New York
- C. J. Lancelot, D. J. Cram and P. v. R. Schleyer. in Carbonium Ions, edited by G. A. Olah and P. v. R. Schleyer, Vol. 3, Chapt. 27, pp. 1347-1483. Wiley, New York (1972).
- (1972) Carbonium Ions , vol.3 , pp. 1347-1483
- Lancelot, C.J.¹ Cram, D.J.² Schleyer, P.V.R.³

31
- 0000856920
- edited by M. Szwarc, Chapt. 3, Wiley, New York
- D. J. Raber, J. M. Harris and P. v. R. Schleyer. in Ions and Ion Pairs in Organic Reactions, edited by M. Szwarc, Vol. 2, Chapt. 3, pp. 247-374. Wiley, New York (1974).
- (1974) Ions and Ion Pairs in Organic Reactions , vol.2 , pp. 247-374
- Raber, D.J.¹ Harris, J.M.² Schleyer, P.V.R.³

32
- 0001277516
- C. Paradisi and J. F. Bunnett. J. Am. Chem. Soc. 103, 946 (1981); 107, 8223 (1985).
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 946
- Paradisi, C.¹ Bunnett, J.F.²

33
- 0000162496
- C. Paradisi and J. F. Bunnett. J. Am. Chem. Soc. 103, 946 (1981); 107, 8223 (1985).
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 8223

34
- 37049090933
- H. J. Koh, H. W. Lee and I. Lee. J. Chem. Soc., Perkin Trans. 2 125 (1994).
- (1994) J. Chem. Soc., Perkin Trans. 2 , pp. 125
- Koh, H.J.¹ Lee, H.W.² Lee, I.³

35
- 11744314579
- M. Fujio, F. Sanematsu, Y. Tsuno, M. Sawada and Y. Takai. Tetrahedron Lett. 29 93 (1988); Y. Tsuji, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1461 (1995); Y. Tsuji, S. H. Kim, Y. Sacki, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1465 (1995); A. D. Allen, M. Fujio, O. S. Tee, T. T. Tidwell, Y. Tsuji, Y. Tsuno and K. Yatsugi. J. Am. Chem. Soc. 117, 8974 (1995).
- (1988) Tetrahedron Lett. , vol.29 , pp. 93
- Fujio, M.¹ Sanematsu, F.² Tsuno, Y.³ Sawada, M.⁴ Takai, Y.⁵

36
- 0028898645
- M. Fujio, F. Sanematsu, Y. Tsuno, M. Sawada and Y. Takai. Tetrahedron Lett. 29 93 (1988); Y. Tsuji, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1461 (1995); Y. Tsuji, S. H. Kim, Y. Sacki, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1465 (1995); A. D. Allen, M. Fujio, O. S. Tee, T. T. Tidwell, Y. Tsuji, Y. Tsuno and K. Yatsugi. J. Am. Chem. Soc. 117, 8974 (1995).
- (1995) Tetrahedron Lett. , vol.36 , pp. 1461
- Tsuji, Y.¹ Yatsugi, K.² Fujio, M.³ Tsuno, Y.⁴

37
- 0028929062
- M. Fujio, F. Sanematsu, Y. Tsuno, M. Sawada and Y. Takai. Tetrahedron Lett. 29 93 (1988); Y. Tsuji, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1461 (1995); Y. Tsuji, S. H. Kim, Y. Sacki, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1465 (1995); A. D. Allen, M. Fujio, O. S. Tee, T. T. Tidwell, Y. Tsuji, Y. Tsuno and K. Yatsugi. J. Am. Chem. Soc. 117, 8974 (1995).
- (1995) Tetrahedron Lett. , vol.36 , pp. 1465
- Tsuji, Y.¹ Kim, S.H.² Sacki, Y.³ Yatsugi, K.⁴ Fujio, M.⁵ Tsuno, Y.⁶

38
- 0000249693
- M. Fujio, F. Sanematsu, Y. Tsuno, M. Sawada and Y. Takai. Tetrahedron Lett. 29 93 (1988); Y. Tsuji, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1461 (1995); Y. Tsuji, S. H. Kim, Y. Sacki, K. Yatsugi, M. Fujio and Y. Tsuno. Tetrahedron Lett. 36, 1465 (1995); A. D. Allen, M. Fujio, O. S. Tee, T. T. Tidwell, Y. Tsuji, Y. Tsuno and K. Yatsugi. J. Am. Chem. Soc. 117, 8974 (1995).
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 8974
- Allen, A.D.¹ Fujio, M.² Tee, O.S.³ Tidwell, T.T.⁴ Tsuji, Y.⁵ Tsuno, Y.⁶ Yatsugi, K.⁷

39
- 0348162714
- Y. Tsuji, Y. Saeki, K. Yatsugi, S.-G. Kim, M. Fujio and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 19, 47 (1993); Y. Tsuji, S.-G Kim, M. Fujio and Y. Tsuno. to be published
- (1993) Mem. Fac. Sci. Kyushu Univ., Ser. C , vol.19 , pp. 47
- Tsuji, Y.¹ Saeki, Y.² Yatsugi, K.³ Kim, S.-G.⁴ Fujio, M.⁵ Tsuno, Y.⁶

40
- 11744386045
- to be published
- Y. Tsuji, Y. Saeki, K. Yatsugi, S.-G. Kim, M. Fujio and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 19, 47 (1993); Y. Tsuji, S.-G Kim, M. Fujio and Y. Tsuno. to be published
- Tsuji, Y.¹ Kim, S.-G.² Fujio, M.³ Tsuno, Y.⁴

41
- 37049055959
- H. P. Crocker and B. Jones. J. Chem. Soc. 1808 (1959).
- (1959) J. Chem. Soc. , pp. 1808
- Crocker, H.P.¹ Jones, B.²

42
- 0006589124
- B. B. P. Tice, I. Lee and F. H. Kendall. J. Am. Chem. Soc. 85, 329 (1963).
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 329
- Tice, B.B.P.¹ Lee, I.² Kendall, F.H.³

43
- 0010403867
- F. G. Bordwell and P. J. Boutan. J. Am. Chem. Soc. 78 87 (1956).
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 87
- Bordwell, F.G.¹ Boutan, P.J.²

44
- 0001175374
- A. C. Cope, E. Ciganek, L. J. Fleckenstein and M. A. P. Meisinger. J. Am. Chem. Soc. 82, 4651 (1960).
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 4651
- Cope, A.C.¹ Ciganek, E.² Fleckenstein, L.J.³ Meisinger, M.A.P.⁴

45
- 0003543590
- Academic Press, New York
- S. R. Sandler and W. Karo. Organic Functional Group Preparations, pp. 325-327. Academic Press, New York (1968).
- (1968) Organic Functional Group Preparations , pp. 325-327
- Sandler, S.R.¹ Karo, W.²

46
- 11744318934
- M. Fujio, K. Ikeda and Y. Tsuno. Mem. Fac. Sci. Kyushu Univ., Ser. C 11, 75 (1978).
- (1978) Mem. Fac. Sci. Kyushu Univ., Ser. C , vol.11 , pp. 75
- Fujio, M.¹ Ikeda, K.² Tsuno, Y.³

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