Acylation and alkylation reactions. Part III. The interaction of aryloxyacetyl chlorides with aluminium chloride in aromatic solvents

Abstract

The proportion of intermolecular acylation to both intramolecular acylation and decarbonylation, during the interaction of aryloxyacetyl chlorides with aluminium chloride in aromatic solvents, increases with the nucleophilic character of the solvent, thus showing the unimolecular nature of carbon monoxide loss. 4-Chlorophenoxy-propionyl and -isobutyryl chlorides undergo decarbonylation more readily than the corresponding acetyl chloride; the products of decarbonylation in some of these reactions are the diarylmethane or cumene rather than the expected diaryl-ethane or -propane.