Lithium cyclopentadienide

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Lithium cyclopentadienide
Names
Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
Identifiers
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Properties
C5H5Li
Molar mass 72.04 g·mol−1
Appearance colorless solid
Density 1.064 g/cm3
decomposition
Solubility THF, dimethoxyethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lithium cyclopentadienide is an

organolithium compound with the formula
C5H5Li. The compound is often abbreviated as LiCp, where Cp is the cyclopentadienide anion. Lithium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities.

Preparation, structure and reactions

Lithium cyclopentadienide is commercially available as a solution in tetrahydrofuran. It is prepared by treating cyclopentadiene with butyllithium:[1]

C5H6 + LiC4H9 → LiC5H5 + C4H10

Because lithium cyclopentadienide is usually handled as a solution, the solvent-free solid is rarely encountered. According to

sandwich complex, consisting of an infinite chain of alternating Li+ centers sandwiched between μ-η5:η5-C5H5 ligands.[2] In the presence of amines or ethers, LiCp gives adducts, e.g. (η5-Cp)Li(TMEDA).[1] LiCp is a common reagent for the preparation of cyclopentadienyl complexes
.

See also

References