Poly(trimethylsilyl)benzenes: Synthese, sulfonation

Abstract

The system Me 3SiCl/Mg/hexamethylphosphorotriamide (HMPT) reacts with some di- or poly-chlorobenzenes leading directly to the corresponding di- or poly-trimethylsilyl derivatives (yields 70-85%). Reaction of trimethylsilyl chlorosulfonate with these compounds gives in a first step trimethylsilyl arylsulfonic esters, Ph(SiMe 3)SO 3SiMe 3. An excess of sulfonating reagent leads to sulfonation either at the PhSi bond (SiMe 3 group in meta or para position) or, mainly, at the MeSi bond (SiMe 3 group in ortho position). By this process new silylated sulfonic compounds can be synthesized.