Reactions of Charged Substrates. 8. The Nucleophilic Substitution Reactions of (4-Methoxybenzyl)dimethylsulfonium Chloride

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 540-551

  Buckley, Neu ^a   Oppenheimer, Norman J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001466756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9620977     Document Type: Article

References (63)

1. 2 provide a fairly complete list of references for the reactions of various benzyl substrates; we will not reproduce that list here.
2. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1990, 112, 9507-9512.
3. Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1996, 61, 7360-7372.
4. Sneen, R. A.; Larsen, J. W. J. Am. Chem. Soc. 1969, 91, 6031-6035.
5. Sneen, R. A.; Felt, G. R.; Dickason, W. C. J. Am. Chem. Soc. 1973, 95, 638-639.
6. Reviewed in Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83-98, and elsewhere. See also Katritzky, A.; Malhotra, N.; Ford, G. P.; Anders, E.; Tropsch, J. G. J. Org. Chem. 1991, 56, 5039-5044.
7. Reviewed in Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83-98, and elsewhere. See also Katritzky, A.; Malhotra, N.; Ford, G. P.; Anders, E.; Tropsch, J. G. J. Org. Chem. 1991, 56, 5039-5044.
8. Kohnstam, G.; Queen, A.; Shillaker, B. Proc. Chem. Soc. 1959, 157-158. See Gregory, B. J.; Kohnstam, G.; Queen, A.; Reid, D. J. Chem. Commun. 1971, 797-799 for a refutation of the arguments made in ref 4.
9. Kohnstam, G.; Queen, A.; Shillaker, B. Proc. Chem. Soc. 1959, 157-158. See Gregory, B. J.; Kohnstam, G.; Queen, A.; Reid, D. J. Chem. Commun. 1971, 797-799 for a refutation of the arguments made in ref 4.
10. (a) Swain, C. G.; Thornton, E. R. J. Org. Chem. 1961, 26, 4808-4809.
11. (b) Swain, C. G.; Taylor, L. J. J. Am. Chem. Soc. 1962, 84, 2456-2457.
12. (c) Swain, C. G.; Rees, T.; Taylor, L. J. J. Org. Chem. 1963, 28, 2903.
13. (d) Swain, C. G.; Burrows, W. D.; Schowen, B. J. J. Org. Chem. 1968, 33, 2534-2536.
14. (e) Swain, C. G.; Kaiser, L. E.; Knee, T. E. C. J. Am. Chem. Soc. 1958, 80, 4092-4094.
15. Kevill, D. N.; Ismail, N. H. J.; D'Sousa, M. J. J. Org. Chem. 1994, 59, 6303-6312.
16. Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1-67; Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. In Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2, Ch. 3. Harris, J. M. Prog. Phys. Org. Chem. 1974, 11, 89-173.
17. Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1-67; Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. In Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2, Ch. 3. Harris, J. M. Prog. Phys. Org. Chem. 1974, 11, 89-173.
18. Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1-67; Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. In Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2, Ch. 3. Harris, J. M. Prog. Phys. Org. Chem. 1974, 11, 89-173.
19. Raber, D. J.; Harris, J. M.; Hall, R. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1971, 93, 4821-4828.
20. (a) Jencks, W. P. Acc. Chem. Res. 1980, 13, 161-169.
21. (b) Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345-375.
22. (c) See Ritchie's excellent explication of the Jencks scheme: Ritchie, C. D. Physical Organic Chemistry: The Fundamental Concepts, 2nd ed.; Dekkar: New York, 1990; pp 132-137.
23. Sneen, R. A. Acc. Chem. Res. 1973, 6, 46-53.
24. Hill, J. W.; Fry, A.J. Am. Chem. Soc. 1962, 84, 2763-2768; Graczyk, D. G.; Taylor, J. W. J. Am. Chem. Soc. 1974, 96, 3255-3261.
25. Hill, J. W.; Fry, A.J. Am. Chem. Soc. 1962, 84, 2763-2768; Graczyk, D. G.; Taylor, J. W. J. Am. Chem. Soc. 1974, 96, 3255-3261.
26. Friedberger, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 2861-2865.
27. Darwish, D.; Hui, S. H.; Tomilson, R. J. Am. Chem. Soc. 1968, 90, 5631-5632.
28. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1383-1396.
29. Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1994, 59, 5717-5723.
30. Buckley, N.; Maltby, D.; Burlingame, A..L.; Oppenheimer, N. J. J. Org. Chem. 1996, 61, 2753-2762.
31. Gregoriou, G. A. Tetrahedron Lett. 1974, 233-237. Dais, P. J.; Gregoriou, G. A. Tetrahedron Lett. 1974, 3827-3831.
32. Gregoriou, G. A. Tetrahedron Lett. 1974, 233-237. Dais, P. J.; Gregoriou, G. A. Tetrahedron Lett. 1974, 3827-3831.
33. Feiser, L.; Feiser, M. L., Reagents for Organic Synthesis; Wiley: New York, 1961; Vol. 1, pp 1180-1181.
34. -1.
35. We thank John Richard for calling this to our attention.
36. Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1994, 59, 247-249.
37. Pearson, R. G. In Advances in Free Energy Relationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1972; pp 281-319.
38. Shiner, V. J. In Isotope Effects in Chemical Reactions; Collins, C. J.; Bowman, N. S., Eds; Van Nostrand Reinhold: New York, 1970; pp 91-159.
39. Ingold, C. K. Structure and Mechanism in Organic Chemistry; Cornell: Ithica, NY, 1953; pp 306-408.
40. Maskill, H. The Physical Basis of Organic Chemistry; Oxford: New York, 1985; p 450.
41. Gould, E. S. Mechanism and Structure in Organic Chemistry; Holt, Rinehart and Winston: New York, 1959; pp 185-187.
42. -1, precisely the partitioning value obtained by Aymes and Richard using a different approach.
43. Meissner, H. P.; Kusik, C. L. Am. Inst. Chem. Eng. J. 1972, 18, 294-298. Meissner, H. P.; Kusik, C. L. Ind. Eng. Chem. Process Des. Develop. 1973, 12, 205-208. Harned, H. S.; Robinson, R. A. Multicomponent Electrolyte Solutions; Pergamon: New York, 1963.
44. Meissner, H. P.; Kusik, C. L. Am. Inst. Chem. Eng. J. 1972, 18, 294-298. Meissner, H. P.; Kusik, C. L. Ind. Eng. Chem. Process Des. Develop. 1973, 12, 205-208. Harned, H. S.; Robinson, R. A. Multicomponent Electrolyte Solutions; Pergamon: New York, 1963.
45. Meissner, H. P.; Kusik, C. L. Am. Inst. Chem. Eng. J. 1972, 18, 294-298. Meissner, H. P.; Kusik, C. L. Ind. Eng. Chem. Process Des. Develop. 1973, 12, 205-208. Harned, H. S.; Robinson, R. A. Multicomponent Electrolyte Solutions; Pergamon: New York, 1963.
46. Fainberg, A. H.; Winstein, S. J. Am. Chem. Soc. 1956, 78, 2763-2767.
47. Maiorova, T. N.; Karpenko, G. V.; Poltoratskii, G. M.; Goverdovskii, B. A.; Krauklis, I. Deposited Document in the Soviet Archive VINITI 3433-77, 193-7, 1977.
48. 2- above the break point are linear (not shown).
49. 1/2 for reactions at constant ionic strength. The two methods give reasonable agreement.
50. Morgan, R. S. J. Chem. Eng. Data 1961, 6, 21-23.
51. Loupy, A.; Tchoubar, B.; Astruc, D. Chem. Rev. 1992, 92, 1141-1165.
52. Swain, C. G.; Kaiser, L. E. J. Am. Chem. Soc. 1958, 80, 4089-4092.
53. 19
54. Hudson, R. F.; Klopman, G. J. Chem. Soc. 1962, 1062-1067.
55. Lyoxide reactions of substituted benzyl dimethyl and phenylmethyl sulfoniums show V-shaped Hammett plots. Schowen, K. B. J. Doctoral Dissertation (MIT, 1964).
56. Richard, J. P.; Yeary, P. E. A Simple Explanation for Curved Hammett Plots for Nucleophilic Substitution Reactions at Ring-Substituted Benzyl Derivatives. Oral presentation at the 206th ACS National Meeting, Chicago, IL, 22-27 August, 1993.
57. Pross, A. Adv. Phys. Org. Chem. 1985, 21, 99-196. Pross, A.; Shaik, S. S. Acc. Chem. Res. 1983, 16, 363-370.
58. Pross, A. Adv. Phys. Org. Chem. 1985, 21, 99-196. Pross, A.; Shaik, S. S. Acc. Chem. Res. 1983, 16, 363-370.
59. 2 before trapping can occur. Because the rate constants for amines and water would be expected to be similar, mere stoichiometry favors water capture. These authors had previously shown
60. 3.
61. Menger, F. M. Tetrahedron 1983, 39, 1013-1040; Menger, F. M. Acc. Chem. Res. 1985, 18, 128-134.
62. Menger, F. M. Tetrahedron 1983, 39, 1013-1040; Menger, F. M. Acc. Chem. Res. 1985, 18, 128-134.
63. Knier, B. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 6789-6796.