Lithium naphthalene

Lithium naphthalene is an organic salt with the chemical formula Li+[C10H8]−.

In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry.

The compound is prepared by stirring the metallic lithium with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane.

[6] With a reduction potential near −2.5 V versus the normal hydrogen electrode, the naphthalene radical anion is a strong reducing agent.

[5] The anion is strongly basic, and a typical degradation pathway involves reaction with water and related protic sources such as alcohols.