Permetalated aromatic compounds, wherein all aromatic hydrogens in an
aromatic molecule are replaced by metal substituents, represent an ext
remely rare class of molecules. A critical examination of the literatu
re might lead to the conclusion that permetalated aromatic compounds p
ossess limited thermodynamic stability due to strong electrostatic rep
ulsion between adjacent carbanionic sites. However, a recent report de
tailing the synthesis of hexalithiobenzene, coupled with recent studie
s on permetalated metallocenes, demonstrate that permetalated aromatic
compounds can possess excellent thermodynamic stability. The present
state of knowledge concerning the structure and reactivity of hexalith
iobenzene, decalithioruthenocene, and decakis(chloromagnesio)ruthenoce
ne is described. The remarkable stability of the existing permetalated
compounds implies that many new permetalated systems should be easily
synthesized.