Potassium 2-germanaphthalenide: an isolable polycyclic system of germanium-incorporated anionic benzenoid

Abstract

We have recently expanded the chemistry of heavy aryl anions, in which the anionic carbon atom of an aryl anion has been replaced with a germanium or tin atom. So far, successful isolation of potassium 2-tert-butylgermabenzenide as a monomer and unexpected trimerization of potassium 9-germaanthracenide have been reported. These results clearly show that the fused benzene ring affects their electronic situation and their tendency toward oligomerization. In this context, we naturally got interested in the case of a naphthalene-based skeleton. Herein, we report the synthesis and isolation of potassium 3-tert-butyl-2-germanaphthalenide, a germanium analogue of 2-naphthylpotassium, as a monomer. Its properties are discussed experimentally and theoretically along with comparisons with the systems of heavy benzene and anthracene.