Chlorine-Substituted Germabenzene: Generation and Application as a Precursor for Aryl-Substituted Germabenzenes

Germabenzene bearing a reactive chlorine group on the germanium atom was generated and characterized by nuclear magnetic resonance spectroscopy. Reactions of the in situ generated chlorogermabenzene with aryllithium reagents gave isolable germabenzenes bearing aryl groups, such as mesityl or acridinyl groups, on the germanium atom. This reaction constitutes the first example for a nucleophilic aromatic substitution of heavy heterobenzenes at the main group center.