Bulletin of the Korean Chemical Society

  • 제10권2호
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  • Pages.151-154
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  • 1989
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Acid-Catalyzed Migration of the Methyl Substituent in the Dienone-Phenol Rearrangement of p-Quinol Ether

  • 발행 : 1989.04.20
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초록

4-Methoxy-4-methylcyclohexa-2,5-dienone 1 in aqueous sulfuric acid underwent the normal dienone-phenol rearrangement with methyl group migration. The fact that methyl is migrating group and methoxy is remaining group can be rationalized by the stabilization of positive charge at C-4 during the transition state. Methoxy methyl dienone 1 $((H_0)_{1/2} = - 4.6)$ is less basic than 4,4-dimethylcyclohexa-2,5-dienone whose half protonation acidity is reported as - 3.15 or - 3.66. This basicity difference comes from the unstabilization of the protonated methoxy methyl dienone 1 due to the electron withdrawing inductive effect of a methoxy group.

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참고문헌

  1. Top. Curr. Chem. v.117 V. G. Schubin
  2. Rearrangements in Ground and Excited States v.1 M. Saunders;J. Chandrasekhar;P. von R. Schleyer;P. de Mayo(ed.)
  3. Mechanisms of Molecular Migrations v.1 B. Miller;B. S. Thyagarajan(ed.)
  4. Adv. Alicyclic Chem. v.1 A. J. Waring
  5. Quart. Rev. v.14 C. J. Collins
  6. Dissertation, Texas Tech University Young-Sook Hahn
  7. J. Am. Chem. Soc. v.96 J. N. Marx;J. C. Argyle;L. R. Norma
  8. J. Am. Soc. Perkin II J.W. Pilkington;A. J. Waring
  9. J. Am. Chem. Soc. v.94 V. P. Vitullo;N. Grossman
  10. J. Am. Chem. Soc. v.79 S. Goodwin;B. Witkop
  11. J. Org. Chem. v.37 V. P. Vitullo;E. A. Logue
  12. J. Org. Chem. v.38 V. P. Vitullo;E. A. Logue
  13. J. Org. Chem. v.41 A. McKillop;D. H. Perry;M. Edwards
  14. J. Am. Chem. Sos. v.91 C. D. Johnson;A. R. Katritzky;S. A. Shapiro
  15. J. Chem. Soc. Perkin II K. L. Cook;A. J. Waring
  16. J. Org. Chem. v.35 V. P. Vitullo
  17. J. Chem. Soc., Perkin II A. J. Waring
  18. J. Am. Chem. Soc. v.61 L. Zucker;L. P. Hammett

피인용 문헌

  1. ChemInform Abstract: Acid‐Catalyzed Migration of the Methyl Substituent in the Dienone‐Phenol Rearrangement of p‐Quinol Ether. vol.20, pp.36, 1989, https://doi.org/10.1002/chin.198936173