Reactions of unsaturated acid halides. Part I. Aluminium chloride-catalysed reactions of phenylpropioloyl chloride with benzene

Abstract

The reaction between benzene and phenylpropioloyl chloride in the presence of aluminium chloride has been re-investigated, and a hydrocarbon, the only previously obtained product, identified as triphenylmethane. Although the simple acylation derivative, phenylpropiolophenone, could not be isolated, by variation in the reaction conditions acetophenone, triphenylmethanol, 9-phenylfluorene, β-phenylchalcone, 3,3-diphenylindanone, and 2,3-diphenyl indone were obtained. The mode of formation of these products is discussed in outline and the reactions of benzene with possible intermediate compounds are reported.