Aluminium chloride catalysed reactions of cinnamoyl chloride with naphthalene, phenanthrene, chrysene and pyrene

Abstract

Homogeneous reactions of cinnamoyl chloride with naphthalene in chlorobenzene and in nitrobenzene in the presence of 1 molar proportion of aluminium chloride give mixtures of 1-naphthyl styryl ketone (1) and 2-naphthyl styryl ketone (2) as initial products. An increase in the molar ratio of (2) to (1) with the time of the reaction at higher temperatures was noted. This variation was shown to be due to subsequent reactions of the cinnamoylnaphthalenes, with (1) reacting more readily than (2), and not due to isomerization of (1) to (2). Reaction of cinnamoyl chloride under similar conditions with phenanthrene, chrysene and pyrene has been examined.