Collect. Czech. Chem. Commun. 1987, 52, 1520-1526

Acylation of ω-phenylalkanoylferrocenes by cinnamoyl and phenylpropiolyl chlorides

Štefan Toma and Marta Sališová

Department of Organic Chemistry, Comenius University, 842 15 Bratislava


In Friedel-Crafts acylation of ω-phenylalkanoylferrocenes, the site of electrophilic attack depends on the reagent used. The acylation with cinnamoyl chloride yields preferentially the products of substitution of the unsubstituted cyclopentadienyl ring of ferrocene. The acylation with phenylpropionyl chloride affords the products of acylation of the benzene ring of the starting compound. The different behaviour of both acylating agents is discussed.