Concerning the Extents of Nucleophilic Participation in Solvolyses of p-Methoxybenzyl Halides

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Dennis N. Kevill and Malcolm J. D'Souza


Abstract

The solvolyses of p-methoxybenzyl chloride (1) in 39 solvents are well correlated using an extended form of the Grunwald–Winstein equation; a claim that nucleophilic participation is greater than in the solvolyses of the corresponding bromide 2 is discussed.


References

  1. K.-T. Liu, Y.-F. Duann and S.-J. Hou, J. Chem. Soc., Perkin Trans. 2, 1998, 2181 RSC.
  2. T. W. Bentley, G. Llewellyn and Z. H. Ryu, J. Org. Chem., 1998, 63, 4654 CrossRef CAS.
  3. D. N. Kevill, N. HJ. Ismail and M. J. D'Souza, J. Org. Chem., 1994, 59, 6303 CrossRef CAS.
  4. T. W. Bentley, J.-P. Dau-Schmidt, G. Llewellyn and H. Mayr, J. Org. Chem., 1992, 57, 2387 CrossRef CAS.
  5. T. W. Bentley, I. S. Koo and S. J. Norman, J. Org. Chem., 1991, 56, 1604 CrossRef CAS.
  6. For reviews of earlier literature, see: A. Streitwieser, Jr., Solvolytic Displacement Reactions, McGraw-Hill, New York, 1962, pp. 40–42 Search PubMed; E. R. Thornton, Solvolysis Mechanisms, Roland Press, New York, 1964, pp. 86–89 Search PubMed.
  7. D. N. Kevill and S. W. Anderson, J. Org. Chem., 1991, 56, 1845 CrossRef CAS.
  8. D. N. Kevill, in Advances in Quantitative Structure–Property Relationships, ed. M. Charton, Jai Press, Greenwich, CN, 1996, vol. 1, pp. 81–115 Search PubMed.
  9. T. W. Bentley and G. Llewellyn, Prog. Phys. Org. Chem., 1990, 17, 121 CAS; D. N. Kevill and M. J. D'Souza, J. Chem. Res. (S), 1993, 174 Search PubMed.
  10. D. N. Kevill and M. J. D'Souza, J. Chem. Soc., Perkin Trans. 2, 1997, 257 RSC and references therein.
  11. M. H. Abraham, P. L. Grellier, J.-L. M. Abboud, R. M. Doherty and R. W. Taft, Can. J. Chem., 1988, 66, 2673 CAS.
  12. K.-T. Liu, J. Chin. Chem. Soc. (Taipei), 1995, 42, 607 CAS; K.-T. Liu and H.-C. Sheu, J. Org. Chem., 1991, 56, 3021 CrossRef CAS.
  13. D. N. Kevill and M. J. D'Souza, J. Chem. Res., 1996, (S) 286; (M) 1649 Search PubMed.
  14. T. W. Bentley and G. E. Carter, J. Am. Chem. Soc., 1982, 104, 5741 CrossRef CAS.
  15. E. Grunwald and S. Winstein, J. Am. Chem. Soc., 1948, 70, 846 CrossRef CAS.
  16. For a brief review, see F. A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry, Brooks/Cole, Pacific Grove, CA, 1998, pp. 360–361 Search PubMed.
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