Elimination of substituted fluoren-9-ylmethyl benzenesulfonates: Hammett substituent effects at a mechanistic borderline

Collection of Czechoslovak Chemical Communications

Volumn 64, Issue 11, 1999, Pages 1833-1848

  Larkin, Finbar G ^a   More O'Ferrall, Rory A ^a   Murphy, Donal G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Base catalysis; E2 and E1cB mechanisms; Hammett relationship; Mechanistic borderline; Reaction kinetics; Eliminations

Indexed keywords

EID: 22844457073     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc19991833     Document Type: Article

References (34)

1. Gandler J. R.: The Chemistry of Double-Bonded Functional Groups (S. Patai, Ed.), Vol. 2, p. 733. Wiley, New York 1989.
2. a) Gandler J. R., Storer W. J., Ohlberg D. A.: J. Am. Chem. Soc. 1990, 112, 7756;
3. b) Gandler J. R.: J. Am. Chem. Soc. 1984, 106, 130.
4. Gandler J. R., Jencks W. P.: J. Am. Chem. Soc. 1982, 104, 1937.
5. a) Thibblin A.: J. Am. Chem. Soc. 1989, 111, 5412;
6. b) Quingshui Meng, Thibblin A.: J. Am. Chem. Soc. 1995, 117, 1839;
7. c) Quingshui Meng, Thibblin A.: J. Am. Chem. Soc. 1995, 117, 9399.
8. a) More O'Ferrall R. A., Warren P. J.: J. Chem. Soc., Chem. Commun. 1975, 483;
9. b) More O'Ferrall R. A., Warren P. J., Ward P. M.: Acta Univ. Uppsol., Symp. Univ. Uppsol. 1978, 12, 209.
10. More O'Ferrall R. A., Larkin F., Walsh P.: J. Chem. Soc., Perkin Trans. 2 1982, 1573.
11. Larkin F., More O'Ferrall R. A.: Aust. J. Chem. 1983, 36, 1831.
12. Thibblin A.: J. Am. Chem. Soc. 1988, 110, 4582.
13. Olwegård M., McEwen I., Thibblin A., Ahlberg P.: J. Am. Chem. Soc. 1985, 107, 7494.
14. Jencks W. P.: Chem. Soc. Rev. 1981, 10, 345.
15. Marshall D. R., Thomas P. J., Stirling C. J. M.: J. Chem. Soc., Perkin Trans. 2 1977, 1914.
16. Banait N. S., Jencks W. P.: J. Am. Chem. Soc. 1990, 112, 6950.
17. a) Thibblin A.: Chem. Soc. Rev. 1993, 427;
18. b) Jencks W. P.: Acc. Chem. Res. 1980, 161;
19. c) Cho B. R., Kim Y. K., Yoon C.-O. M.: J. Am. Chem. Soc. 1997, 119, 691;
20. d) Richard J. P., Jencks W. P.: J. Am. Chem. Soc. 1988, 110, 4582;
21. e) Koch H. F., Lodder G., Koch J. G., Bogdon D. J., Brown G. H., Carlson C. A., Dean A. B., Hage R., Han P., Hopman J. C. P., James L. A., Knape P. M., Roos E. C., Sardina M. L., Dawyer R. A., Scott B. O., Testa C. A., III, Wickham S. D.: J. Am. Chem. Soc. 1997, 119, 9965.
22. Bordwell F. G., Drucker G. E., McCollum G. J.: J. Org. Chem. 1976, 41, 2786.
23. Koch H. F.: Personal communication.
24. Gilbert E. E.: Synthesis 1969, 3.
25. Prinsen A. J., Cerfontain H.: Rec. Trav. Chim. Pays-Bas 1965, 84, 22.
26. Meerwein H., Dittmar G., Gollner R., Hafner K., Mensch F., Steinfort O.: Chem. Ber. 1957, 90, 84.
27. Yale H. L., Sowinski F.: J. Org. Chem. 1960, 25, 1824.
28. Banger J., Cockerill A. F., Davis G. L. O.: J. Chem. Soc. B 1971, 498.
29. Exner O.: Advances in Free Energy Relationships (N. B. Chapman and J. Shorter, Eds), p. 1. Plenum, London 1972.
30. Kevill D. N., Kolwyck K. C., Shold D. M., Kim C.-B.: J. Am. Chem. Soc. 1973, 95, 6022.
31. Hoefnagel A. J., Hoefnagel M. A., Wepster B. M.: J. Org. Chem. 1976, 41, 2786.
32. a) King J. F., Rathore R.: J. Am. Chem. Soc. 1990, 112, 2001;
33. b) Li M., King J. F.: Fifth International Conference on Heteroatom Chemistry, London, Canada, July 1998. Abstracts p. 32.
34. Walsh P. A.: Ph.D. Thesis. National University of Ireland, Dublin 1976.