Kinetics and mechanism of the aminolysis of O-aryl S-methyl thiocarbonates

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2679-2685

  Castro, Enrique A ^a   Aliaga, Margarita ^a   Santos, José G ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; IONIC STRENGTH; PH EFFECTS; RATE CONSTANTS; SPECTROPHOTOMETRY;

AMINOLYSIS; QUINUCLIDINES (QUI); SECONDARY ALICYCLIC (SA); THIOCARBONATE;

AROMATIC COMPOUNDS;

1 (2 HYDROXYETHYL)PIPERAZINE; 1 FORMYLPIPERAZINE; 2,3,4,5,6 PENTAFLUOROPHENYLMETHYLTHIOCARBONATE; 2,4 DINITROPHENYLMETHYLTHIOCARBONATE; 3 CHLOROQUINUCLIDINE; 3 QUINUCLIDINOL; 3 QUINUCLIDINONE; 4 NITROPHENYLMETHYLTHIOCARBONATE; AMINE; AMPHOLYTE; CARBONIC ACID DERIVATIVE; ION; MORPHOLINE; PIPERAZINE; PIPERAZINIUM ION; PIPERIDINE; POTASSIUM CHLORIDE; QUINUCLIDINE; QUINUCLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINOLYSIS; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); IONIC STRENGTH; PH; REACTION ANALYSIS; SPECTROPHOTOMETRY; TEMPERATURE;

EID: 17044428979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047742l     Document Type: Article

References (42)

1. (a) Fife, T. H.; Hutching, J. E. C. J. Am. Chem. Soc. 1972, 94, 2837.
2. (b) Fife, T. H.; Hutchins, J. E. C. J. Am. Chem. Soc. 1981, 103, 4194.
3. (c) Koh, H. J.; Lee, J. W.; Lee, H. W.; Lee, I. Can. J. Chem. 1998, 76, 710.
4. (a) Bond, P. M.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1976, 679.
5. (b) Castro, E. A.; Gil, F. J. J. Am. Chem. Soc. 1977, 99, 7611.
6. (c) Castro, E. A.; Freudenberg, M. J. Org. Chem. 1980, 45, 906.
7. (d) Castro, E. A.; Ibañez. F.; Lagos, S.; Schick, M.; Santos, J. G. J. Org. Chem. 1992, 57, 2691.
8. (a) Castro, E. A.; Ibañez, F.; Saitúa, A. M.; Santos, J. G. J. Chem. Res., Synop. 1993, 56.
9. (b) Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 2001, 66, 6000.
10. (c) Castro, E. A.; Aliaga, M.; Campodónico, P.; Santos J. G. J. Org. Chem. 2002, 67, 8911.
11. Castro, E. A. Chem. Rev. 1999, 99, 3505.
12. (a) Castro, E. A.; Ibáñez, F.; Salas, M.; Santos, J. G. J. Org. Chem. 1991, 56, 4819.
13. (b) Castro, E. A.; Salas, M.; Santos, J. G. J. Org. Chem. 1994, 59, 30.
14. (c) Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1994, 59, 3572.
15. (d) Castro, E. A.; Muñoz, P.; Santos, J. G. J. Org. Chem. 1999, 64, 8298.
16. Castro, E. A.; Aliaga, M.; Santos J. G., J. Org. Chem. 2004, 69, 6711.
17. Castro, E. A.; Ureta, C. J. Org. Chem. 1989, 54, 2153.
18. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963.
19. Pianka, M. J. J. Sci. Food Agric. 1966, 17, 47. Huang, T. L.; Szekacs, A.; Uematsu, T.; Kurvano, E.; Parkinson, A.; Hammock, B. D. Pharm. Research 1993, 10, 639.
20. Pianka, M. J. J. Sci. Food Agric. 1966, 17, 47. Huang, T. L.; Szekacs, A.; Uematsu, T.; Kurvano, E.; Parkinson, A.; Hammock, B. D. Pharm. Research 1993, 10, 639.
21. (a) Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018.
22. (b) Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1987, 109, 6362.
23. Castro, E. A.; Ureta, C. J. Chem. Soc., Perkin Trans. 2 1991, 63.
24. Bell, R. P. The Proton in Chemistry; Methuen: London, 1959; p 159.
25. 14 For the title reactions, it means that in the TS for the first step, bond formation is well advanced relative to charge development
26. Jencks, W. P. Chem. Rev. 1985, 85, 511. Williams, A. Acc. Chem. Res. 1984, 17, 425. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
27. Jencks, W. P. Chem. Rev. 1985, 85, 511. Williams, A. Acc. Chem. Res. 1984, 17, 425. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
28. Jencks, W. P. Chem. Rev. 1985, 85, 511. Williams, A. Acc. Chem. Res. 1984, 17, 425. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
29. Jencks, W. P. Chem. Rev. 1985, 85, 511. Williams, A. Acc. Chem. Res. 1984, 17, 425. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
30. Castro, E. A.; Cubillos, M.; Aliaga, M.; Evangelisti, S.; Santos, J. G. J. Org. Chem. 2004, 69, 2411.
31. (a) Castro, E. A.; Ibañez, F.; Salas, M.; Santos, J. G.; Sepulveda, P. J. Org. Chem. 1993, 58, 459.
32. (b) Castro, E. A.; Araneda, C. A.; Santos, J. G. J. Org. Chem. 1997, 62, 126.
33. Castro, E. A.; Ureta, C. J. Org. Chem. 1990, 55, 1676.
34. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
35. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6970.
36. Castro, E. A.; Pizarro, M. I.; Santos, J. G. J. Org. Chem. 1996, 61, 5982.
37. Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 1999, 64, 2310.
38. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants; Chapman and Hall: London, 1971; p 87.
39. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345. Williams, A. Acc. Chem. Res. 1989, 22, 387.
40. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345. Williams, A. Acc. Chem. Res. 1989, 22, 387.
41. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345. Williams, A. Acc. Chem. Res. 1989, 22, 387.
42. Castro, E. A.; Cubillos, M.; Santos, J. G.; Tellez, J. J. Org. Chem. 1997, 62, 2512.