Kinetics and Mechanism of the Aminolysis of Phenyl and 4-Nitrophenyl Chlorothionoformates

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4395-4397

  Castro, Enrique A ^a   Cubillos, María ^a   Santos, José G ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001060560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970276y     Document Type: Article

References (28)

1. Kevill, D. N. In The Chemistry of Acyl Halides; Patai, S., Ed.; Interscience: New York, 1972; p 381.
2. Queen, A. Can. J. Chem. 1967, 45, 1619. Moodie, R. B.; Towill, R. J. Chem. Soc., Perkin Trans. 2 1972, 184. Koo, I. S.; Yang, K.; Kang, K.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 1996, 17, 520.
3. Queen, A. Can. J. Chem. 1967, 45, 1619. Moodie, R. B.; Towill, R. J. Chem. Soc., Perkin Trans. 2 1972, 184. Koo, I. S.; Yang, K.; Kang, K.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 1996, 17, 520.
4. Queen, A. Can. J. Chem. 1967, 45, 1619. Moodie, R. B.; Towill, R. J. Chem. Soc., Perkin Trans. 2 1972, 184. Koo, I. S.; Yang, K.; Kang, K.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 1996, 17, 520.
5. Olofson, R. A. Pure Appl. Chem. 1988, 60, 1715. Kevill, D. N.; Kyong, J. B. J. Org. Chem. 1992, 57, 258.
6. Olofson, R. A. Pure Appl. Chem. 1988, 60, 1715. Kevill, D. N.; Kyong, J. B. J. Org. Chem. 1992, 57, 258.
7. (a) Hall, H. K., Jr. J. Am. Chem. Soc. 1957, 79, 5439.
8. (b) Castro, E. A.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1974, 658.
9. (c) Bond, P. M.; Castro, E. A.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1976, 68.
10. Yew, K. H.; Koh, H. J.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1995, 2263.
11. Castro, E. A.; Ureta, C. J. Org. Chem. 1989, 54, 2153.
12. Hilgetag, G.; Philippson, R. Monatsber. Deut. Akad. Wiss. Berlin 1964, 6, 585; Chem. Abstr. 1965, 62, 5165h.
13. Hilgetag, G.; Philippson, R. Monatsber. Deut. Akad. Wiss. Berlin 1964, 6, 585; Chem. Abstr. 1965, 62, 5165h.
14. Bell, R. P. The Proton in Chemistry, Methuen: London, 1959; p 159.
15. Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018.
16. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963.
17. Palling, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 4869.
18. Castro, E. A.; Ureta, C. J. Chem. Soc., Perkin Trans. 2 1991, 63.
19. Castro, E. A.; Ibáñez, F.; Salas, M.; Santos, J. G.; Sepúlveda, P. J. Org. Chem. 1993, 58, 459.
20. Castro, E. A.; Cubillos, M..; Santos, J. G. J. Org. Chem. 1994, 59, 3572. Castro, E. A.; Pizarro, M. I.; Santos, J. G. J. Org. Chem. 1996, 61, 5982.
21. Castro, E. A.; Cubillos, M..; Santos, J. G. J. Org. Chem. 1994, 59, 3572. Castro, E. A.; Pizarro, M. I.; Santos, J. G. J. Org. Chem. 1996, 61, 5982.
22. Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1996, 61, 3501.
23. Hammett, L. P. Physical Organic Chemistry, 2nd ed; McGraw-Hill: New York, 1970; p 358.
24. Castro, E. A.; Ibáñez, F.; Santos, J. G.; Ureta, C. J. Org. Chem. 1993, 58, 4908.
25. Castro, E. A.; Cubillos, M.; Muñoz, G.; Santos, J. G. Int. J. Chem. Kinet. 1994, 26, 571.
26. Sayer, J. M.; Jencks, W. P. J. Am. Chem. Soc. 1973, 95, 5637. Fox, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 1436.
27. Sayer, J. M.; Jencks, W. P. J. Am. Chem. Soc. 1973, 95, 5637. Fox, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 1436.
28. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.