Kinetics and mechanism of the aminolysis of cycloalkylmethyl arenesulfonates

Journal of Physical Organic Chemistry

Volumn 10, Issue 2, 1997, Pages 91-96

  Oh, Hyuck Keun ^a   Song, Se Jeong ^a   Jo, Dong Soo ^b   Lee, Ikchoon ^b  

^a Chonbuk National University   (South Korea)

^b Inha University   (South Korea)

Author keywords

Cycloalkylmethyl arenesulfonates; Nucleophilic substitution reactions; Positive xz values; Secondary kinetic isotope effects

Indexed keywords

EID: 0442287618     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199702)10:2<91::AID-POC862>3.0.CO;2-M     Document Type: Article

References (16)

1. (a) I. Lee, Chem. Soc. Rev. 19, 317-333 (1990)
2. (b) I. Lee, Adv. Phys. Org. Chem. 27, 57-117 (1992)
3. (c) I. Lee, Chem. Soc. Rev. 24, 223-229 (1995).
4. I. Lee, J. Phys. Org. Chem. 5, 736-740 (1992).
5. I. Lee, C. K. Kim, D. S. Chung and B.-S. Lee, J. Org. Chem. 59, 4490-4494 (1994).
6. H. K. Oh, Y. B. Kwon, D. S. Chung and I. Lee, Bull Korean Chem. Soc. 16, 827-831 (1995).
7. H. K. Oh, Y. B. Kwon, H. J. Koh and I. Lee, J. Phys. Org. Chem. in press.
8. H. K. Oh, Y B. Kwon, I. H. Cho and I. Lee, J. Chem. Soc., Perkin Trans. 2 1697-1701 (1994).
9. R. W. Taft, Jr, in Steric Effects in Organic Chemistry, edited by M. S. Newman, Chapt. 13. Wiley, New York (1956).
10. M. J. S. Dewar and R. C. Dougherity, The PMO Theory of Organic Chemistry, p. 212-222. Plenum Press, New York (1975).
11. I. Lee, H. J. Koh, B.-S. Lee, D. S. Sohn and B. C. Lee, J. Chem. Soc., Perkin Trans. 2 1741-1746 (1991).
12. I. Lee, H. K. Kang and H. W. Lee, J. Am. Chem. Soc. 109, 7472-7477 (1987).
13. R. D. Gilliom, Introduction to Physical Organic Chemistry, p. 148. Addison-Wesley, London (1970).
14. W. C. Davis and W. Addis, J. Chem. Soc. 1622 (1937); G. Thomson, J. Chem. Soc. 1113 (1946).
15. W. C. Davis and W. Addis, J. Chem. Soc. 1622 (1937); G. Thomson, J. Chem. Soc. 1113 (1946).
16. R. V. Hoffman and J. M. Shankweiler, J. Am. Chem. Soc. 108, 5536 (1986).