Tetraethylammonium-p-toluene

An example of dimerization of the intermediates of an electrode reaction is provided by the reduction of acrylonitrile in a sufficiently concentrated aqueous solution of tetraethylammonium p-toluene sulphonate at a mercury or lead electrode. The intermediate in the reaction is probably the dianion... 

Shono et al. (1979) recommend the use of thioanisole as a catalyst that allows lowering the electrode potential in the oxidation of the secondary alcohols into ketones. The cation-radical of thioanisole is generated at a potential of up to +1.5 V in acetonitrile containing pyridine (Py) and a secondary alcohol. (The background electrolyte was tetraethylammonium p-toluene sulfonate.) Thioanisole is recovered and, therefore, a ratio of RXR )CHOH PhSMe = 1 0.2 is sufficient. The yield of ketones depends on the nature of the alcohol and varies from 70 to 100%. 

Thus, acrylonitrile (an example of activated olefin) yields cathodically a coupling reaction (adiponitrile) in aqueous solution (use of quaternary salts) containing tetraethylammonium p-toluene sulfonate, which provides a hydrophobic thin layer at the cathode interface [189,190], This process first designed with a divided cell was transformed to... 

All chemicals, if not otherwise mentioned, were reagent grade and used without further purification. Polymerization solutions consisted of pyrrole monomer (Sigma Chemical Company) dopant electrolyte (tetraethylammonium-p-toluene) sulphonate, Alfa/Aldrich Chemical Company) and distilled water. The ratio of pyrrole dopant concentration was maintained at 3 1, as this has previously been found to be optimum, and the initial pyrrole concentration was 0.75 moll. ... 

The unsaturated nucleoside (53) has been prepared in good yield by electrochemical elimination from either the 2 -bromo-arabino- or the 3-bromo-xylo-nucleoside indicated in Scheme 14 however, the electrolyte can control the product obtained, for whereas 2-bromo-2 -deoxy-3, 5-di-O-propanoyl-uracil gave the 2, 3-unsaturated nucleoside in presence of tetraethylammonium toluene-p-sulphonate in methanol, with sodium acetate a mixture of products was obtained 3-deoxy-3-iodo-adenosine yielded 3-deoxy-adenosine (cordycepin) besides the 2, 3-unsaturated nucleoside.1-Acetyl-glycenose derivatives have been condensed with purine and pyrimidine derivatives in presence of antimony... 

Di-iododimethylsilane appears to be an effective reagent for the mild deoxygenation of a-arylalkanols to the corresponding hydrocarbon. Aliphatic alcohol methanesulphonates are selectively reduced in good yield by an electrochemical method. The reaction is performed in a divided cell with a lead cathode and a platinum anode in dry DMF containing tetraethylammonium toluene-p-sulphonate. Yields are in the range 57—87%, and groups such as esters, olefins, nitriles, and even epoxides are inert under these conditions. ... 

---