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5.3.25.6.1 Variation 1: From Metal Tetraalkylborates or Tetraalkylaluminates

DOI: 10.1055/sos-SD-005-00813

Eagle, P. A. C.Science of Synthesis, (20035784.

Symmetrical tetraalkylplumbanes can be obtained by the electrolysis of sodium tetra­alkylborates in aqueous solution[‌62‌] or sodium tetraalkylaluminates or alkylalkoxyaluminates in ethereal solvents[‌63‌] at a lead anode. A mercury pool is required as the counter electrode at which metallic byproducts redissolve. For example, tetramethylplumbane is obtained in an estimated 90% yield, by the electrolysis of sodium tetramethylaluminate in tetrahydrofuran at a lead anode in a cylindrical cell (Figure 1). A potential difference of 5.5V is maintained between the anode and the mercury electrode giving a cell current of 3.8A (Scheme 8).[‌63‌] The requirement for a mercury cathode in this approach has obvious environmental disadvantages and an alternative route to tetraethylplumbane involves the electrolysis of potassium dichloro(diethyl)aluminate and ethyl chloride in a sealed cell using a platinum counter electrode.[‌64‌] Here the alkyl halide is believed to react with aluminum metal produced at the anode, preventing its deposition within the cell.

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