Aromatic substitution of olefins. Part XVIII. Reactions of cycloalkenes with benzene

Abstract

The reactions of cyclopentene, cyclohexene, cycloheptene, and cyclo-octene with benzene in the presence of palladium(II) acetate have been investigated. The reaction with cyclo-octene, for example, gave the substitution product, 1 -phenylcyclo-octene (6%), and the isomerisation products, 3-phenyl-(8%), 4-phenyl-(12%), and 5-phenyl-cyclo-octene (2%). In general the substitution reactions are complicated by isomerisation or disproportionation processes.