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・ Sodium maleonitriledithiolate
・ Sodium manganate
・ Sodium metabisulfite
・ Sodium metaborate
・ Sodium metatitanate
・ Sodium metavanadate
・ Sodium methanethiolate
・ Sodium methoxide
・ Sodium methylparaben
・ Sodium methylsulfinylmethylide
・ Sodium molybdate
・ Sodium monofluorophosphate
・ Sodium monothiophosphate
・ Sodium myreth sulfate
・ Sodium myristate
Sodium naphthalenide
・ Sodium nitrate
・ Sodium nitride
・ Sodium nitrite
・ Sodium nitroprusside
・ Sodium nonanoyloxybenzenesulfonate
・ Sodium orthophenyl phenol
・ Sodium orthovanadate
・ Sodium oxalate
・ Sodium oxide
・ Sodium oxybate
・ Sodium pareth sulfate
・ Sodium perborate
・ Sodium percarbonate
・ Sodium perchlorate


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Sodium naphthalenide : ウィキペディア英語版
Sodium naphthalenide

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Sodium naphthalenide, also known as sodium naphthalide, is an organic salt with the formula Na+C10H8. 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.〔 N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. 〕
==Preparation and properties==
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. 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 463, 735 nm.〔
The anion is strongly basic, and a typical degradation pathway involves reaction with water and related protic sources. These reactions afford dihydronaphthalene:
:2 NaC10H8 + 2 H2O → C10H10 + C10H8 + 2 NaOH

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