Hard Acid and Soft Nucleophile System. VII. A Convenient Reduction of Functionalized Polyarenes to Parent Polyarenes

Abstract

Oxygen functions and halogens at the peri-carbon atom in polyarenes were reductively removed with the AlCl₃-EtSH reagent system to afford the parent polyarenes in high yield. The reaction consists of two steps of reactions involving displacement of a functionality with an alkylthio group followed by reductive removal of the introduced alkylthio moiety. A radical cation induced mechanism for the latter process is proposed on the basis of several observations.