Sodium naphthalenide

Sodium naphthalenide, also known as sodium naphthalide, is a soluble one-electron reductant employed in organic, organometallic, and inorganic chemistry. [cite journal | doi = 10.1021/ja01627a017 | title = Reducing Action of Sodium Naphthalide in Tetrahydrofuran Solution. I. The Reduction of Cobalt(II) Chloride | year = 1955 | author = Ting, Li Chu; Joseph V. Friel | journal = J. Am. Chem. Soc.| volume = 77 | pages = 5838] [cite journal | doi = 10.1021/ja01642a004 | title = The Magnetic Susceptibilities of Some Aromatic Hydrocarbon Anions | year = 1954 | author = Ting, Li Chu; Yu, Shan Chi | journal = J. Am. Chem. Soc.| volume = 76 | pages = 3367] It is prepared by stirring sodium metal with naphthalene in a polar solvent such as tetrahydrofuran or dimethoxyethane, resulting in the formation of a dark green solution. [OrgSynth | prep=cv8p0093 | author = E. J. Corey and Andrew W. Gross | title = "tert"-Butyl-"tert"-octylamine | collvol = 8 | collvolpages = 93 | year = 1993] It cannot be stored as a solid, so it must be prepared fresh immediately before use.

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