Ester Aminolysis. Structure-Reactivity Relationships and the Rate-Determining Step in the Aminolysis of Substituted Diphenyl Carbonates

Journal of the American Chemical Society

Volumn 99, Issue 21, 1977, Pages 6963-6970

  Gresser, M J ^a   Jencks, W P ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847090104     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00463a032     Document Type: Article

References (25)

1. W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc., 90, 2622 (1968).
2. A. Satterthwait and W. P. Jencks, J. Am. Chem. Soc., 96, 7018 (1974).
3. A. Satterthwait and W. P. Jencks, J. Am. Chem. Soc., 96, 7031 (1974).
4. G. G. Smith and B. Kosters, Chem. Ber., 93, 2400 (1960).
5. T. C. Bruice, A. Donzel, R. W. Huffman, and A. R. Butler, J. Am. Chem. Soc., 89, 2106 (1967).
6. J. F. Kirsch and W. P. Jencks, J. Am. Chem. Soc., 86, 837 (1964).
7. D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc., 99, 451 (1977).
8. J. M. Sayer and W. P. Jencks, J. Am. Chem. Soc., 99, 464 (1977).
9. P. M. Bond, E. A. Castro, and R. B. Moodie, J. Chem. Soc., Perkin Trans. 2, 68 (1976).
10. S. Osterman-Golkar, L. Ehrenberg, and F. Solymosy, Acta Chem. Scand., B28, 215 (1974).
11. J. M. Sayer and W. P. Jencks, J. Am. Chem. Soc., 95, 5637 (1973).
12. J. P. Fox and W. P. Jencks, J. Am. Chem. Soc., 96, 1436 (1974).
13. C. D. Ritchie and W. F. Sager, Prog. Phys. Org. Chem., 2, 323 (1964).
14. A. R. Fersht and W. P. Jencks, J. Am. Chem. Soc., 92, 5432 (1970).
15. A. R. Fersht and Y. Requena, J. Am. Chem. Soc., 93, 3499 (1971);
16. A. R. Fersht, J. Am. Chem. Soc., 93, 3504 (1971).
17. W. P. Jencks, B. Schaffhausen, K. Tornheim, and H. White, J. Am. Chem. Soc., 93, 3917 (1971).
18. M. J. Gresser and W. P. Jencks, J. Am. Chem. Soc., following paper in this issue.
19. A. R. Butler, I. H. Robertson, and R. Bacaloglu, J. Chem. Soc., Perkin Trans. 2, 1733(1974). The value of β1g=-0.21 is the ratio of the p values of 0.47 for log k and-2.2 for the pK of substituted phenols (G. H. Parsons and C. H. Rochester, J. Chem. Soc., Faraday Trans. 1, 71, 1058 (1975)). There is evidence that the reaction of pyridine with chloroformates involves rate-determining attack.10
20. C. K. Sauers, W. P. Jencks, and S. Groh, J. Am. Chem. Soc., 97, 5546 (1975).
21. J. Gerstein and W. P. Jencks, J. Am. Chem. Soc., 86, 4655 (1964).
22. S. L. Johnson, Adv. Phys. Org. Chem., 5, 237 (1967).
23. A. R. Fersht and W. P. Jencks, J. Am. Chem. Soc., 92, 5442 (1970).
24. C. D. Ritchie, J. Am. Chem. Soc., 97, 1170 (1975).
25. D. G. Oakenfull and W. P. Jencks, J. Am. Chem. Soc., 93, 178 (1971).