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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 2
BKCSDE 10(2)
February 20, 1989

Title	Acid-Catalyzed Migration of the Methyl Substituent in the Dienone-Phenol Rearrangement of p-Quinol Ether
Author	Young-Sook Paik Hahn
Keywords
Abstract	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 ((H0)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.
Page	151 - 154
Full Text	PDF

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