Journal of the Chemical Society. Perkin transactions II p. 907 - 913 (1990)
Update date:2022-08-28
Topics:
Jackson, Lorraine B.
Waring, Anthony J.
Studies have been made of the reactions with nucleophiles of 4-benzoyl-4-methylcyclohexa-2,5-dienone and its 4-chlorobenzoyl- and 4-methoxybenzoyl- analogues.Water effects hydrolysis to 4-methylphenol and the appropriate substituted benzoic acid.Kinetic measurements give a log kobs vs. pH profile with slopes close to -1.0, 0, and 1.0, indicating proton, water, and hydroxide ion catalysis, respectively.The results suggest a mechanistic pattern similar to that found for the cleavage of benzaldehyde hemiacetals.Alcohols and alkoxides effect analogous cleavage to 4-methylphenol and the alkyl benzoates.Reaction of the 4-benzoyl-4-methylcyclohexa-2,5-dienone with dialkyl amines gives varying proportions of 4-methylphenyl benzoate and 4-methylphenol with N,N-dialkylbenzamide.An initial amine-induced rearrangement of the dienone to 4-methylphenyl benzoate is followed by cleavage by the amine to give the phenol and amide.
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