A drastic effect of halide anions on the nucleophilic substitution of 1-phenylbenzo[b]thiophenium salts

Abstract

Nucleophilic substitution of 1,2,3-triarylbenzo[b]thiophenium salts with halide anions (Cl^– and Br^–) has been found to yield 2,3-diarylbenzo[b]thiophenes, halobenzenes and 1,2-diaryl-1-halo-2-[2-(phenylsulfanyl)phenyl]ethenes and especially the reaction with iodide anion gives only 2,3-diarylbenzo[b]thiophenes and iodobenzene, indicating that halide anions behave quite differently from the reaction with alkoxide anions reported previously.