99234-42-1Relevant articles and documents
Synthesis of 4-Benzoyl-4-methylcyclohexa-2,5-dienone and its Benzoyl Substitued Derivatives: Isolated 4-Acylcyclohexa-2,5-dienones
Jackson, Lorraine B.,Waring, Anthony J.
, p. 1791 - 1798 (2007/10/02)
The synthesis are reported of 4-benzoyl-4-methylcyclohexa-2,5-dienone, and its 4-(4-chlorobenzoyl) and 4-(4-methoxybenzoyl) analogues.These are the first isolated 4-acylcyclohexa-2,5-dienones containing the dienone function in a monocyclic ring system.All are sensitive to nucleophilic attack at the benzoyl carbonyl group, being cleaved to 4-methylphenol and its derivatives of the appropriate substitued benzoic acid.Treatment with acids failed to give the desired dienone-phenol rearrangement, with a benzoyl migration from C-4 to C-3, but instead gave 4-methylphenyl benzoate or its derivatives, by a reversal of a Fries rearrangement with C-4 to O-aroyl migration.