Journal of the Chemical Society. Perkin transactions II p. 1893 - 1898 (1990)
Update date:2022-08-16
Topics:
Jackson, Lorraine B.
Waring, Anthony J.
4-Benzoyl-4-methylcyclohexa-2,5-dienone is known as one of the few relatively stable 4-acylcyclohexa-2,5-dienones.In attempts to achieve dienone-phenol rearrangements with acyl migration it has been treated with Lewis acids and with non-nucleophilic acids in non-polar solvents.In each case rapid acil migration occurs to give 4-methylphenyl benzoate by a retro-Fries rearrangement, along with some cleavage to the phenol.The benzoyl group can be trapped by another phenol, and the mechanism is formulated as a dissociation-recombination process with significant leakage of the 4-methylphenol and benzoyl cation.The reaction is compared with the Fries/retro-Fries equilibrium which has been induced between phenyl esters and 2- and 4-acyl phenols.Observations are made on the photochemical Fries rearrangement of 4-methylphenyl acetate, which has been suggested to proceed via 4-acetyl-4-methylcyclohexa-2,5-dienone, and of 4-methylphenyl benzoate.
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