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Acid-Catalyzed Migration of the Methyl Substituent in the Dienone-Phenol Rearrangement of p-Quinol Ether
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  • Acid-Catalyzed Migration of the Methyl Substituent in the Dienone-Phenol Rearrangement of p-Quinol Ether
  • Acid-Catalyzed Migration of the Methyl Substituent in the Dienone-Phenol Rearrangement of p-Quinol Ether
저자명
Paik Hahn. Young-Sook
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1989년|10권 2호|pp.151-154 (4 pages)
발행정보
대한화학회
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정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

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.