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Deprotonation of dibenzo-N-tert-butylaminofulvene leads to the (1-azapentadienyl)lithium derivative eta-5-azapentadienyllithium being readily available. The derivative is also obtainable from the mechanistically more complex reaction sequence sparked off by treatment of the aminomethylfluorene derivative 9-(N-tert-butylaminomethyl)-fluorene with suitable bases. There seem to be energetic limits to the Li-1-azapentadienyl bonding interaction of eta-5-azapentadienyllithium.

Examines the structure and chemical behavior of the eta5-(1-azapentadienyl)lithium derivative. Identification of eta5-(1-azapentadienyl)lithium derivative as a global minimum; Analysis of the bonding features of the dilithiated system; Mechanism of the generation of the derivative by deprotonation reactions.