Synthesis and reactions of some cyclohexadienones. Part II

Merchant, J. R. ; Desai, V. B. (1968) Synthesis and reactions of some cyclohexadienones. Part II Journal of the Chemical Society C: Organic . pp. 499-503. ISSN 0022-4952

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The synthesis of 4-alkyl-4-trihalogenomethylcyclohexa-2,5-dienone derivatives by the application of the Zincke-Suhl reaction on p-alkyl-phenols is described. In some cases, only benzophenone derivatives were obtained. When the dienones were treated with reagents like phosphorus pentachloride and sulphuric acid, migration of the groups from the gem-C-atom occurred giving rise to halogenated benzoic acid derivatives which were identified in most cases by their synthesis by independent routes. In a few cases elimination of the alkyl group was also observed during reaction with phosphorus pentachloride.

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