sodium naphthalene sulfonate formaldehyde (SNF/PNS)

タイトルまたは説明

Sodium naphthalenide, also known as sodium naphthalide, is an organic salt with the formula Na+C*0H8−. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It has not been isolated as a solid, but it is usually prepared fresh before use.[1]

Preparation and properties[edit]
The alkali metal naphthalenides are prepared by stirring the metal with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane. The resulting salt is dark green.[2][3][4] The anion is a radical, giving a strong EPR signal near g = 2.0, with a reduction potential near *2.5 V vs NHE. Its deep green color arises from absorptions centered at **3, **5 nm.[1]

The anion is strongly basic, and a typical degradation pathway involves reaction with water and related protic sources. These reactions afford dihydronaphthalene:

2 NaC*0H8 + 2 H2O → C*0H*0 + C*0H8 + 2 NaOH
Related reagents[edit]
For some synthetic operations, sodium naphthalenide is excessively reducing (too negative), in which case milder reductants are selected. Larger rings give milder reductants. Sodium acenaphthenide is milder by about 0.*5 V.

The corresponding lithium salt, lithium naphthalenide, is also known.