Kinetics of the Reactions of Benzylidene Meldrum's Acid with Thiolate and Alkoxide Ions in Aqueous Dimethyl Sulfoxide

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6266-6272

  Bernasconi, Claude F ^a   Ketner, Rodney J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000864080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980574a     Document Type: Article

References (67)

1. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
2. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
3. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
4. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
5. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
6. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
7. For reviews, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
8. (a) Bernasconi, C. F.; Fassberg, J.; Killion, R. B., Jr.; Rappoport, Z. J. Am. Chem. Soc. 1989, 111, 6862.
9. (b) Bernasconi, C. F.; Fassberg, J.; Killion, R. B., Jr.; Rappoport, Z. J. Am. Chem. Soc. 1990, 112, 3169.
10. (a) Bernasconi, C. F.; Schuck, D. F.; Ketner, R. J.; Weiss, M.; Rappoport, Z. J. Am. Chem. Soc. 1994, 116, 11764.
11. (b) Bernasconi, C. F.; Schuck, D. F.; Ketner, R. J.; Eventova, I.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 2719.
12. (a) Bernasconi, C. F.; Leyes, A. E.; Rappoport, Z.; Eventova, I. J. Am. Chem. Soc. 1993, 115, 7513.
13. (b) Bernasconi, C. F.; Leyes, A. E.; Eventova, I.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 1703.
14. Bernasconi, C. F.; Ketner, R. J.; Chen, X.; Rappoport, Z. J. Am. Chem. Soc. 1998, 120, 7461.
15. Bernasconi, C. F.; Ketner, R. J.; Chen, X.; Rappoport, Z. To be published.
16. Eigen, M.; Ilgenfritz, G.; Kruse, W. Chem. Ber. 1965, 98, 1623.
17. Bernasconi, C. F.; Oliphant, N. Unpublished results.
18. 10,11
19. (a) Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870.
20. (b) Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1988, 110, 1872.
21. See also: Arnett, E. M.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1987, 109, 809.
22. 13
23. Bernasconi, C. F.; Kliner, D. A. V.; Mullin, A. S.; Ni, J. X. J. Org. Chem. 1988, 53, 3342.
24. Bernasconi, C. F.; Killion, R. B., Jr. J. Am. Chem. Soc. 1988, 110, 7506.
25. Bernasconi, C. F.; Fassberg, J. J. Am. Chem. Soc. 1994, 116, 514.
26. Bernasconi, C. F.; Leonarduzzi, G. D. J. Am. Chem. Soc. 1980, 102, 1361.
27. 2O) ≪ 1.
28. (a) Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 554.
29. (b) Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions, Wiley: New York, 1963; p 156.
30. Jencks, W. P. Chem. Rev. 1985, 85, 511.
31. -8.
32. Bernasconi, C. F.; Keiner, R. J. To be published.
33. (a) Hine, J.; Weimar, R, D., Jr. J. Am. Chem. Soc. 1965, 87, 3387.
34. (b) Hine, J. Structural Effects on Equilibria in Organic Chemistry; Wiley-Interscience; New York, 1975; p 226.
35. Ritchie, C. D.; Gandler, J. R. J. Am. Chem. Soc. 1979, 101, 7318.
36. (a) Kallen, R. G.; Jencks, W. P. J. Biol. Chem. 1966, 241, 5864.
37. (b) Lienhard, G. E.; Jencks, W. P. J. Am. Chem. Soc. 1966, 88, 3982.
38. (c) Sander, E. G.; Jencks, W. P. J. Am. Chem. Soc, 1968, 90, 6154.
39. (a) Pearson, R. G.; Songstad, J. J. Am. Chem. Soc. 1967, 89, 1827.
40. (b) Pearson, R. G. Survey Prog. Chem. 1969, 5, 1.
41. (a) Parker, A. J. J. Chem. Rev. 1969, 69,1.
42. (b) Bordwell, F. G.; Hughes D. L. J. Org. Chem. 1982, 47, 3224.
43. (c) Taft, R. W. Prog. Phys. Org. Chem. 1983, 14, 247.
44. (a) Kresge, A. J. Chem. Soc. Rev. 1979, 2, 475.
45. (b) Jencks, W. P.; Brant, S. R.; Gandler, J. R.; Fendrich, G. Nakamura, C. J. Am. Chem. Soc. 1982, 104, 7045.
46. 19
47. Kresge, A. J. Acc. Chem. Res. 1975, 8, 354.
48. (a) Pross, A. J. Org. Chem. 1984, 49, 1811.
49. (b) Bordwell, F. G.; Hughes, D. L. J. Am. Chem., Soc. 1985, 107, 4737,
50. (c) Pross, A.; Shaik, S. S. New J. Chem. 1989, 13, 427.
51. Bernasconi, C. F.; Schuck, D. F. J. Org. Chem. 1992, 57, 2365.
52. Gilbert, H. F.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 7931.
53. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451.
54. Friedman, M.; Cavins, J. F.; Wall, J. S. J. Am. Chem. Soc. 1965, 87, 3672.
55. Santala, T.; Fishbein, J. C. J. Am. Chem. Soc. 1992, 114, 8852.
56. (a) Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
57. (b) Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
58. (c) Cohen, A. O.; Marcus, R. A. J. Phys. Chem. 1968, 72, 4249.
59. N2-type substitution rather than an addition reaction.
60. Hupe, D. J.; Pohl, E. R. Isr. J. Chem. 1985, 26, 395.
61. 40 states that if development of a product-stabilizing factor lags behind, or the loss of a reactant stabilizing factor is ahead of bond changes at the transition state, the intrinsic rate constant is lowered. Examples of such stabilizing factors include resonance and solvation. On the other hand, if a product-stabilizing factor develops early, or a reactant-stabilizing factor is lost late, the intrinsic rate constant is enhanced.
62. (a) Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301.
63. (b) Bernasconi C. F. Acc. Chem. Res. 1992, 25, 9.
64. (c) Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
65. Schuster, P.; Polansky, O. E.; Wessely, F. Monatsch. Chem. 1964, 95, 53.
66. Hallé, J.; Gaboriaud, R.; Schaal, R. Bull. Soc. Chim. Fr. 1970, 2047.
67. Program by Robin J. Leatherbarrow (Department of Chemistry, Imperial College of Science & Technology, South Kensington, London SW7 2A4, U.K.). Published and distributed by BIOSOFT, 22 Hills Road, Cambridge CB2 1JP, U.K.