Sodium naphthalide, electron-transfer reactions

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. 

In the course of an extensive study of the mode of action of anionic catalysts, A. G. Evans used exclusively h.v.t. His investigation of the electron-transfer reactions involving 1,1,3,3-tetraphenylbutene-l, tetraphenylethylene and sodium naphthalide is of particular interest here because all the reaction mixtures were prepared by h.v.t. and both UV and ESR spectra were measured (J. E. Bennett et al, 1963). The paper contains full experimental details. 

Some interesting electron-transfer reactions of sodium naphthalide have recently been reported. Reaction with phenylmercuric chloride or benzylmercuric chloride gives better than 70% yields of the symmetric diphenyl- or dibenzylmercury compounds. Solutions of alkali metals in HMPA lead to the same results (88). Evidence for the reaction of sodium naphthalide with methylene halides to give methylene anion radical, CH2T, has recently appeared (22). 

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-... 

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