ELECTROPHILIC SUBSTITUTION OF BENZENES WITH STRONG ELECTRON-WITHDRAWING GROUPS IN SUPER ACID MEDIA. FRIEDEL-CRAFTS ALKYLATION OF ACETOPHENONE

In the presence of HF-SbF5 super acid, the alkylation of acetophenone with various alkyl chlorides was investigated. The products were found to be those of m-alkylated acetophenone derivatives and their related compounds in fairly good yields. The relative reactivity of alkyl chlorides was in the order of EtCl>n-, iso-PrCl, n-, s-BuCl>>iso-BuCl>>t-BuCl. The formation of olefinic, alcoholic, and condensation products observed in the reaction with propyl chlorides, and skeletal isomerization products obtained in the reaction with butyl chlorides was also discussed.