DOI QR코드

DOI QR Code

Solvation in Mixed Solvents (IV). Solvolysis of Adamantyl Derivatives in Methanol-Acetonitrile Mixtures

  • Published : 1985.02.20

Abstract

Solvolysis of 1-adamantyl chloride, -bromide and -tosylate have been studied in methanol-acetonitrile mixtures. Rate maxima were found for 1-adamantyl bromide and tosylate at 80-90 % methanol mixtures. The rate maximum observed was interpreted as a result of cooperative enhancement of cation and anion solvation. 1-Adamantyl tosylate had small cation solvation but had extensive anion solvation. It was concluded that the Y scale based on adamantyl tosylate is superior to others since it varies in a wide range especially for weakly ionizing medium.

Keywords

References

  1. J. Amer. Chem. Soc. v.70 E. Grunwald;S. Winstein
  2. J. Amer. Chem. Soc. v.92 D. J. Raber;R. C. Bingham;J. M. Harris;J. L. Fry;P. v. R. Schleyer
  3. J. Amer. Chem. Soc. v.83 P. v. R. Schleyer;R. D. Nicholas
  4. J. Amer. Chem. Soc. v.92 D. N. Kevill;K. C. Kolwyck;F. L. Weitl
  5. J. Chem. Soc., Chem. Commun. D. N. Kevill;M. S. Bahari
  6. J. Amer. Chem. Soc. v.106 D. N. Kevill;M. S. Bahari;S. W. Anderson
  7. J. Chem. Soc., Perkin trans. v.2 P. R. Luton;M. C. Whiting
  8. Tetrahedron Letters D. N. Kevill;F. Weitl
  9. J. Chem. Soc., Chem. Commun. H. Maskill;J. T. Thompson;A. A. Wilson
  10. Purification of Laboratory Chemicals(2nd ed.) D. D. Perrin;W. L. F. Armarego;D. R. Perrin
  11. J. Chem. Soc. (B) J. MacMillan;R. J. Pryce
  12. J. Amer. Chem. Soc. v.73 S. Winstein;E. Grunwald;H. W. Jones
  13. Phil. Mag. v.2 E. A. Guggenheim
  14. Prog. Phys. Org. Chem. v.13 M. J. Kamlet;J. L. M. Abboud;R. W. Taft
  15. J. Org. Chem. v.49 R. W. Taft;J. L. M. Abboud;M. J. Kamlet
  16. J. Korean Chem. Soc. v.28 I. Lee;S. La;B-S. Lee;S. C. Sohn
  17. Intern. J. Quant. Chem. v.23 J. Bertran;A. Lledos;J. A. Revetllat
  18. J. Org. Chem. v.48 T. W. Bentley;G. E. Carter
  19. J. Amer. Chem. Soc. v.79 A. H. Fainberg;S. Winstein
  20. J. Chem. Soc. L. J. Le Roux;E. R. Swart
  21. Tetrahedron Letters J. Kaspi;Z. Rappoprt
  22. J. Chem. Soc., Faraday Trans., I v.78 T. W. Bentley;G. E. Carter
  23. Bull. Korean Chem. Soc. v.4 I. Lee;B-S. Lee;I. S. Koo;S. C. Sohn
  24. J. Amer. Chem. Soc. v.104 T. W. Bentley;G. E. Carter
  25. J. Amer. Chem. Soc. v.79 C. G. Swain;R. B. Mosely

Cited by

  1. Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile–methanol mixtures vol.1995, pp.12, 1985, https://doi.org/10.1039/p29950002257