Solvolysis of tert-Butyl(2-naphthyl)methyl and Some Benzhydryl Bromides. A New Y Scale for Benzylic Bromides with Extended Charge Delocalisation†

(Note: The full text of this document is currently only available in the PDF Version )

Kwang-Ting Liu, Chien-Pu Chin, Yen-Shyi Lin and Meng-Lin Tsao


Abstract

The necessity of establishing a new Y xBnBr scale based on log k values for tert-butyl(2-naphthyl)methyl bromide is demonstrated by the results of correlation analysis of solvolytic reactivities of benzhydryl bromides and 4-nitrobenzhydryl bromide.


References

  1. E. Grunwald and S. Winstein, J. Am. Chem. Soc., 1948, 70, 846 CrossRef CAS.
  2. S. Winstein, E. Grunwald and H. W. Jones, J. Am. Chem. Soc., 1951, 73, 2700 CrossRef CAS.
  3. K.-T. Liu, J. Chin. Chem. Soc., 1995, 42, 607 CAS and references cited therein.
  4. K.-T. Liu, H.-Y. Hsu and J.-S. Yang, Tetrahedron Lett., 1992, 33, 3327 CrossRef CAS.
  5. K.-T. Liu, C.-P. Chin, Y.-S. Lin and M.-L. Tsao, Tetrahedron Lett., 1995, 36, 6919 CrossRef CAS.
  6. D. N. Kevill, N. HJ. Ismail and M. J. D'Souza, J. Org. Chem., 1994, 59, 6303 CrossRef CAS.
  7. D. N. Kevill and M. J. D'Souza, J. Chem. Soc., Perkin Trans. 2, 1995, 973 RSC.
  8. D. N. Kevill and M. J. D'Souza, J. Chem. Res., 1996, (S) 286; (M) 1649 Search PubMed.
  9. K.-T. Liu, J. Chem. Soc., Perkin Trans. 2, 1996, 327 RSC.
  10. T. W. Bentley and G. Llewellyn, Progr. Phys. Org. Chem., 1990, 17, 121 Search PubMed.
  11. J. C. Miller and J. N. Miller, Statistics for Analytical Chemistry, Wiley, New York, 2nd edn., 1988, ch. 3 Search PubMed.
  12. (a) D. N. Kevill and S. W. Anderson, J. Chem. Res. (S), 1991, 356 Search PubMed; (b) D. N. Kevill and M. J. D'Souza, J. Chem. Res. (S), 1993, 174 Search PubMed.
  13. D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon, New York, 3rd edn., 1988 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.