Reducing agents sodium naphthalide

Sodium anthracenide and potassium acenaphthylenide have been used. They are much milder reducing agents than naphthalides, for example ... 

Even the chemically robust perfluoroalkanes can undergo electron-transfer reactions (equation 4) because of their relatively high electron affinities [89]. Strong reducing agents like alkali metals [90] or sodium naphthalide [91] are normally required for reaction, but perfluoroalkanes with low-energy, tert-C-F 0 anti-... 

This procedure is based on that previously described by Wilke.1 The use of NaBH4 and sodium naphthalide as reducing agents has been more recently reported by Ugo.2... 

Metal carbonyl anions can be derived by reduction, e.g. reactions 23.16-23.21 dimers such as Mn2(CO)io and Co2(CO)g undergo simple cleavage of the M—M bond, but in other cases, reduction is accompanied by an increase in metal nuclearity. In reactions 23.16 and 23.21 NapioHg] (sodium naphthalide) is made from Na and naphthalene both Na[CioH8] and K[CioH8] are powerful reducing agents. 

In either case, a single initiator can now propagate chains from both ends by virtue of its two active endgroup carbanions. These reactions are heterogeneous and involve transfer of the electron from the surface of the metal. To improve the efficiency of this process, soluble reducing agents such as sodium naphthalide are used. Sodium undergoes electron-transfer reactions with extended aromatic compounds, such as naphthalene, to form soluble radical anions. 

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