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Abstract
Permetalated aromatic compounds, wherein all aromatic hydrogens in an aromatic molecule are replaced by metal substituents, represent an extremely rare class of molecules. A critical examination of the literature might lead to the conclusion that permetalated aromatic compounds possess limited thermodynamic stability due to strong electrostatic repulsion between adjacent carbanionic sites. However, a recent report detailing the synthesis of hexalithiobenzene, coupled with recent studies on permetalated metallocenes, demonstrate that permetalated aromatic compounds can possess excellent thermodynamic stability. The present state of knowledge concerning the structure and reactivity of hexalithiobenzene, decalithioruthenocene, and decakis(chloromagnesio)ruthenocene is described. The remarkable stability of the existing permetalated compounds implies that many new permetalated systems should be easily synthesized.