Pure Appl. Chem., 2009, Vol. 81, No. 4, pp. 685-696
http://dx.doi.org/10.1351/PAC-CON-08-08-11
Kinetics and mechanism of the aminolysis of thioesters and thiocarbonates in solution
References
- 1. (a). W. P. Jencks. Prog. Phys. Org. Chem. 2, 63 (1964); (http://dx.doi.org/10.1002/9780470171813.ch2)
- 1. (b). S. L. Johnson. Adv. Phys. Org. Chem. 5, 237 (1967); (http://dx.doi.org/10.1016/S0065-3160(08)60312-3)
- 1. (c). A. C. Satterthwait, W. P. Jencks. J. Am. Chem. Soc. 96, 7018 (1974); (http://dx.doi.org/10.1021/ja00829a034)
- 1. (d). C. D. Johnson. Chem. Rev. 75, 755 (1975); (http://dx.doi.org/10.1021/cr60298a004)
- 1. (e). A. J. Kirby. In Organic Reaction Mechanisms, A. C. Knipe, W. E. Watts (Eds.), pp. 29-83, John Wiley, New York (1980); (http://dx.doi.org/10.1002/9780470318973.ch2)
- 1. (f). J. P. Guthrie. Acc. Chem. Res. 16, 122 (1983); (http://dx.doi.org/10.1021/ar00088a002)
- 1. (g). R. A. McClelland, L. J. Santry. Acc. Chem. Res. 16, 394 (1983); (http://dx.doi.org/10.1021/ar00095a001)
- 1. (h). A. Williams. Adv. Phys. Org. Chem. 27, 1 (1992); (http://dx.doi.org/10.1016/S0065-3160(08)60063-5)
- 1. (i). K. Bowden. Adv. Phys. Org. Chem. 28, 171 (1993); (http://dx.doi.org/10.1016/S0065-3160(08)60182-3)
- 1. (j). A. Williams. Chem. Soc. Rev. 23, 93 (1994); (http://dx.doi.org/10.1039/cs9942300093)
- 1. (k). K. Bowden. Chem. Soc. Rev. 24, 431 (1995); (http://dx.doi.org/10.1039/cs9952400431)
- 1. (l). W. P. Jencks. J. Phys. Org. Chem. 9, 337 (1996). (http://dx.doi.org/10.1002/(SICI)1099-1395(199606)9:6<337::AID-POC803>3.0.CO;2-P)
- 2. (a). H. J. Koh, J. W. Lee, H. W. Lee, I. Lee. Can. J. Chem. 76, 710 (1998); (http://dx.doi.org/10.1139/cjc-76-6-710)
- 2. (b). E. A. Castro, M. Aliaga, P. Campodonico, J. G. Santos. J. Org. Chem. 67, 8911 (2002); (http://dx.doi.org/10.1021/jo026390k)
- 2. (c). P. Tundo, L. Rossi, A. Loris. J. Org. Chem. 70, 2219 (2005); (http://dx.doi.org/10.1021/jo048532b)
- 2. (d). E. A. Castro, M. Gazitua, J. G. Santos. J. Org. Chem. 70, 8088 (2005); (http://dx.doi.org/10.1021/jo051168b)
- 2. (e). I.-H. Um, E. Y. Kim, H.-R. Park, S.-E. Jeon. J. Org. Chem. 71, 2302 (2006); (http://dx.doi.org/10.1021/jo052417z)
- 2. (f). I.-H. Um, Y.-M. Park, M. Fujio, M. Mishima, Y. Tsuno. J. Org. Chem. 72, 4816 (2007); (http://dx.doi.org/10.1021/jo0705061)
- 2. (g). G.-Q. Yi, Y. Zeng, X.-F. Xia, Y. Xue, C.-K. Kim, G.-S. Yan. Chem. Phys. 348, 73 (2008); (http://dx.doi.org/10.1016/j.chemphys.2008.01.036)
- 2. (h). E. A. Castro, C. Soto, B. Vasquez, J. G. Santos. Arkivoc X, 151 (2008).
- 3. (a). E. A. Castro. Chem. Rev. 99, 3505 (1999); (http://dx.doi.org/10.1021/cr990001d)
- 3. (b). E. A. Castro. J. Sulfur Chem. 28, 401 (2007). (http://dx.doi.org/10.1080/17415990701415718)
- 4. (a). D. D. Sung, I. S. Han, I. Lee. J. Sulfur Chem. 28, 483 (2007); (http://dx.doi.org/10.1080/17415990701490950)
- 4. (b). I.-H. Um, S. Yoon, H.-R. Park, H.-J. Han. Org. Biomol. Chem. 6, 1618 (2008). (http://dx.doi.org/10.1039/b801422a)
- 5. (a). E. A. Castro, C. Ureta. J. Org. Chem. 54, 2153 (1989); (http://dx.doi.org/10.1021/jo00270a026)
- 5. (b). E. A. Castro, C. Ureta. J. Chem. Soc., Perkin Trans. 2, 63 (1991). (http://dx.doi.org/10.1039/p29910000063)
- 6. (a). E. A. Castro, F. Ibanez, M. Salas, J. G. Santos. J. Org. Chem. 56, 4819 (1991); (http://dx.doi.org/10.1021/jo00016a002)
- 6. (b). E. A. Castro, M. Cubillos, J. G. Santos. J. Org. Chem. 59, 3572 (1994). (http://dx.doi.org/10.1021/jo00092a014)
- 7. (a). E. A. Castro, M. Aliaga, J. G. Santos. J. Org. Chem. 69, 6711 (2004); (http://dx.doi.org/10.1021/jo048935b)
- 7. (b). E. A. Castro, M. Aliaga, J. G. Santos. J. Org. Chem. 70, 2679 (2005). (http://dx.doi.org/10.1021/jo047742l)
- 8. E. A. Castro, M. Aliaga, J. G. Santos. J. Phys. Org. Chem. 21, 271 (2008). (http://dx.doi.org/10.1002/poc.1312)
- 9. (a). E. A. Castro, M. I. Pizarro, J. G. Santos. J. Org. Chem. 61, 5982 (1996); (http://dx.doi.org/10.1021/jo960781f)
- 9. (b). E. A. Castro, L. Leandro, P. Millan, J. G. Santos. J. Org. Chem. 64, 1953 (1999). (http://dx.doi.org/10.1021/jo982063u)
- 10. E. A. Castro, P. Munoz, J. G. Santos. J. Org. Chem. 64, 8298 (1999). (http://dx.doi.org/10.1021/jo991036g)
- 11. (a). E. A. Castro, R. Aguayo, J. Bessolo, J. G. Santos. J. Org. Chem. 70, 3530 (2005); (http://dx.doi.org/10.1021/jo050119w)
- 11. (b). E. A. Castro, M. Vivanco, R. Aguayo, J. G. Santos. J. Org. Chem. 69, 5399 (2004); (http://dx.doi.org/10.1021/jo049260f)
- 11. (c). E. A. Castro, R. Aguayo, J. Bessolo, J. G. Santos. J. Phys. Org. Chem. 19, 555 (2006). (http://dx.doi.org/10.1002/poc.1055)
- 12. (a). E. A. Castro, L. Leandro, J. G. Santos. Int. J. Chem. Kinet. 31, 839 (1999); (http://dx.doi.org/10.1002/(SICI)1097-4601(1999)31:12<839::AID-KIN1>3.0.CO;2-#)
- 12. (b). M. Cabrera, E. A. Castro, M. Salas, J. G. Santos, P. Sepulveda. J. Org. Chem. 56, 5324 (1991); (http://dx.doi.org/10.1021/jo00018a022)
- 12. (c). E. A. Castro, M. Cabrera, J. G. Santos. Int. J. Chem. Kinet. 27, 49 (1995); (http://dx.doi.org/10.1002/kin.550270107)
- 12. (d). E. A. Castro, F. Ibanez, J. G. Santos, C. Ureta. J. Chem. Soc., Perkin Trans. 2 1919 (1991); (http://dx.doi.org/10.1039/p29910001919)
- 12. (e). E. A. Castro, F. Ibanez, J. G. Santos, C. Ureta. J. Org. Chem. 57, 7024 (1992). (http://dx.doi.org/10.1021/jo00052a010)
- 13. (a). E. A. Castro, M. Cubillos, J. G. Santos. J. Org. Chem. 61, 3501 (1996); (http://dx.doi.org/10.1021/jo951726u)
- 13. (b). E. A. Castro, J. G. Santos, J. Tellez, M. I. Umana. J. Org. Chem. 62, 6568 (1997); (http://dx.doi.org/10.1021/jo970624w)
- 13. (c). E. A. Castro, F. Ibanez, J. G. Santos, C. Ureta. J. Org. Chem. 58, 4908 (1993). (http://dx.doi.org/10.1021/jo00070a028)
- 14. (a). E. A. Castro, F. Ibanez, M. Salas, J. G. Santos, P. Sepulveda. J. Org. Chem. 58, 459 (1993); (http://dx.doi.org/10.1021/jo00054a033)
- 14. (b). E. A. Castro, G. Munoz, M. Salas, J. G. Santos. Int. J. Chem. Kinet. 27, 987 (1995); (http://dx.doi.org/10.1002/kin.550271004)
- 14. (c). E. A. Castro, M. Cubillos, G. Munoz, J. G. Santos. Int. J. Chem. Kinet. 26, 571 (1994). (http://dx.doi.org/10.1002/kin.550260510)
- 15. M. J. Gresser, W. P. Jencks. J. Am. Chem. Soc. 99, 6963 (1977). (http://dx.doi.org/10.1021/ja00463a032)
- 16. R. P. Bell. The Proton in Chemistry, p. 159, Methuen, London (1959).
- 17. (a). W. P. Jencks. Acc. Chem. Res. 13, 161 (1980); (http://dx.doi.org/10.1021/ar50150a001)
- 17. (b). W. P. Jencks. Chem. Soc. Rev. 10, 345 (1981); (http://dx.doi.org/10.1039/cs9811000345)
- 17. (c). A. Williams. Acc. Chem. Res. 22, 387 (1989). (http://dx.doi.org/10.1021/ar00167a003)
- 18. M. J. Gresser, W. P. Jencks. J. Am. Chem. Soc. 99, 6970 (1977). (http://dx.doi.org/10.1021/ja00463a033)
- 19. (a). I.-H. Um, J.-S. Min, H.-W. Lee. Can. J. Chem. 77, 659 (1999); (http://dx.doi.org/10.1139/cjc-77-5-6-659)
- 19. (b). I.-H. Um, J.-S. Min, J.-A. Ahn, H.-J. Han. J. Org. Chem. 65, 5659 (2000); (http://dx.doi.org/10.1021/jo000482x)
- 19. (c). I.-H. Um, S.-J. Hwang, M.-H. Baek, E.-J. Park. J. Org. Chem. 71, 9191 (2006). (http://dx.doi.org/10.1021/jo061682x)
- 20. W. P. Jencks, M. Gilchrist. J. Am. Chem. Soc. 90, 2622 (1968). (http://dx.doi.org/10.1021/ja01012a030)
- 21. (a). J. M. Sayer, W. P. Jencks. J. Am. Chem. Soc. 95, 5637 (1973); (http://dx.doi.org/10.1021/ja00798a031)
- 21. (b). J. P. Fox, W. P. Jencks. J. Am. Chem. Soc. 96, 1436 (1974). (http://dx.doi.org/10.1021/ja00812a029)
- 22. C. Hansch, A. Leo, R. W. Taft. Chem. Rev. 91, 165 (1991). (http://dx.doi.org/10.1021/cr00002a004)
- 23. P. J. Taylor. J. Chem. Soc., Perkin Trans. 2 1423 (1993). (http://dx.doi.org/10.1039/p29930001423)
- 24. M. Eigen. Angew. Chem., Int. Ed. Engl. 3, 1 (1964). (http://dx.doi.org/10.1002/anie.196400011)
- 25. S. V. Hill, S. Thea, A. Williams. J. Chem. Soc., Perkin Trans. 2 437 (1983). (http://dx.doi.org/10.1039/p29830000437)