DOI QR코드

DOI QR Code

Reactions of Aryl Halides with Phenoxides and Alkoxides by Phase Transfer Catalysis

  • 조봉래 (고려대학교 이과대학 화학과) ;
  • 박성대 (고려대학교 이과대학 화학과)
  • Published : 1984.06.20

Abstract

The reaction of aryl halides with phenoxides and alkoxides were investigated under phase transfer catalytic conditions. 2,4-Dinitro- and 4-nitrohalobenzenes reacted readily with phenoxides in NaOH(aq)-benzene in the presence of Bu4N+Br, affording the products quantitatively. Although the aryl halides did not react with alkoxides under the same condition, the reactions were completed within 2 hours at room temperature when conducted under solid-liquid phase transfenr catalytic condition. The reactivity of aryl halides was in the order, Ar = 2,4-dinitrophenyl > 4-nitrophenyl, and X = F > Cl, consistent with the SNAr mechanism. The reactivity of oxyanions increased with the change of reaction condition from liquid-liquid to solid-liquid phase transfer catalysis. The results were explained with the concentration and the degree of hydration of the anion in benzene.

Keywords

References

  1. Phase Transfer Catalysis C. M. Stark;C. Liotta
  2. Polymer. (Korea) v.7 J.-I. Jin;J.-H. Chang;B. R. Cho
  3. J. Amer. Chem. Soc. v.97 A. W. Harriott;D. Picker
  4. Quart, Rev. v.12 J. F. Bunnett
  5. Lange Handbook of Chemistry(12th Ed.) Dean
  6. J. Amer. Chem. Soc. R. W. Bost;F. Nicholson
  7. J. Amer. Chem. Soc. v.48 L. C. Raiford;J. C. Colbert
  8. Polymer (Koresa) v.7 B. R. Cho;S. D. Park;J. I. Jin
  9. Phase Transfer Catalysis in Organic Synthesis W. P. Weber;G. W. Gokel
  10. The Chemist's Companion A. J. Gordon;R. A. Ford
  11. J. Chem. Soc., Perkin II R. C. Michael;G. Brenda;W. C. Francis
  12. J. Chem. Res. D.A.Ahmad;R.C.Michael

Cited by

  1. Solid-Liquid Phase Transfer Catalysis Without Solvent: Further Improvement in SNAr Reactions vol.20, pp.18, 1990, https://doi.org/10.1080/00397919008051499