Kinetics of the solvolyses of fluoro-substituted benzhydryl derivatives: Reference electrofuges for the development of a comprehensive nucleofugality scale

European Journal of Organic Chemistry

Volumn , Issue 8, 2010, Pages 01435-1439

  Nolte, Christoph ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Carbocations; Kinetics; Linear free relationships; Nucleophilic substitution; Solvent effects

Indexed keywords

EID: 77649219689     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901400     Document Type: Article

References (36)

1. For reviews on carbocations, see: a) A. Streitwieser Jr. Solvolytic Displacement Reactions. McGraw-Hill. New York, 1962:
2. b) Carbonium Ions (Eds.: G. A. Olah. P. v. R. Schleyer), Interscience. New York, 1968-1976, vols. 1-5;
3. c) P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985;
4. d) Advances in Carbocalion Chemistry (Ed.: X. Creary), JAI Press, Greenwich. CT. 1989, vol.1:
5. e) Advances in Carbocalion Chemistry (Ed.: J. M. Coxon), JAI Press. Greenwich. CT. 1995. vol.2;
6. f) A. R. Katritzky, Chem. Soc. Rev. 1990. 19. 83-105;
7. g) R. A. McClelland in Reactive Intermediate Chemistry (Eds.: R. A. Moss. M. S. Platz, M. Jones Jr), Wiley-Interscience, Hoboken, NJ. 2004, chapter 1.
8. a) http://www.cup.lmu.de/oc/mayr/DBintro.html:
9. b) H. Mayr. T. Bug. M. F. Gotta. N. Hering. B. Irrgang, B. Janker, B. Kempf, R. Loos. A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512:
10. c) H. Mayr. A. R. Ofial, Pure Appl. Chem. 2005, 77, 1807-1821;
11. d) H. Mayr, A. R. Ofial. J. Phys. Org. Chem. 2008, 21, 584-595:
12. e) H. Mayr, M. Patz, Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957;
13. f) H. Mayr. B. Kempf, A. R. Ofial. Acc. Chem. Res. 2003, 36, 66-77.
14. a) B. Denegri, A. Streiter, S. Juric, A. R. Ofial, O. Kronja, H. Mayr, Chem. Eur. J. 2006, 12, 1648-1656;
15. Corrigenda: B. Denegri, A. Streiter, S. Juric, A. R. Ofial, O. Kronja, H. Mayr, Chem. Eur. J. 2006, 12, 5415;
16. b) B. Denegri, A. R. Ofial, S. Juric, A. Streiter, O. Kronja, H. Mayr, Chem. Eur. J. 2006, 12, 1657-1666;
17. c) B. Denegri, O. Kronja, J. Org. Chem. 2007, 72, 8427-8433;
18. d) B. Denegri, O. Kronja, J. Phys. Org. Chem. 2009, 22. 495-503:
19. e) B. Denegri, O. Kronja. J. Org. Chem. 2009, 74, 5927-5933.
20. C. Sailer, J. Ammer, C. Noite, I. Pugliesi, H. Mayr, E. Riedle, lecture presented at the XXIV Int. Conf. on Photochemistry, Toledo, Spain, 2009.
21. For a review on the preparation and application of sulfonates, see: P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85-102.
22. G. W. H. Cheeseman, R. C. Poller. J. Chem. Soc. 1962, 5277-5280.
23. W. T. Bentley, M. Christi, S. J. Norman. J. Org Chem. 1991, 50, 6240-6243.
24. For reviews on common-ion rate depression, see: a) D. J. Raber, J. M. Harris, P. v. R. Schleyer in Ions and Ion Pairs in Organic Reactions (Ed.: M. Szwarc), Wiley, New York, 1974, vol.2;
25. b) P. J. Stang, Z. Rappoport, M. Hanack, L. R. Subramanian, Vinyl Cations, Academic Press, New York, 1979, chapter 6, pp. 337-338;
26. c) Z. Rappoport in Reactive Intermediates (Ed.: R. A. Abramovitch), Plenum Press, New York, 1983, vol.3, pp. 583-594;
27. d) T. Kitamura, H. Taniguchi, Y. Tsuno in Dicoordinated Carbocations (Eds.: Z. Rappoport. P. J. Stang). Wiley, Chichester, UK, 1997, pp. 321-376.
28. a) G. R. Cowie, H. J. M. Fitches, G. Kohnstam, J. Chem. Soc. 1963. 1585-1593;
29. b) J. R. Fox. G. Kohnstam, J. Chem. Soc. 1963, 1593-1598.
30. a) J. R. Fox, G. Kohnstam, Proc. Chem. Soc. London 1964, 115-116;
31. b) S. Nishida. J. Org. Chem. 1967, 32, 2692-2695;
32. c) S. Nishida, J. Org. Chem. 1967, 32, 2695-2697;
33. d) S. Nishida, J. Org. Chem. 1967, 32, 2697-2701:
34. e) Y. Tsuno, M. Fujio. Adv. Phys. Org. Chem. 1999, 32, 267-385.
35. C. Hansch, A. Leo. R. W. Taft. Chem. Rev. 1991, 91, 165-195.
36. C. Schade, H. Mayr. Tetrahedron 1988, 44, 5761-5770.