Abstract

Acylation of methyl and benzylethers of orcinol with the same ethers of phloroglucinol carboxylic acid using trifluoroacetic anhydride (TFAA) in chloroform or dichloro methane afforded both unsymmetrical and symmetrical benzophenones. Magnetic resonance measurements were performed on the reactions between various deuterium labelled methylethers of phloroglucinol and phloroglucinol carboxylic acid. The reaction was found to proceed via several equilibria resulting in a total scrambling of the aromatic rings around the carbonyl function. The occurrence of an intermediate in the reaction was observed and is thought to consist of an ion pair between a protonated benzophenone and trifluoroacetate ion which rapidly catalyses an exchange between TFAA and TFA.

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