Tetramethylammonium reductions, electrolytic

Another important factor in electroreduction is the electrolyte. Most electrolytic reductions are carried out in more or less dilute sulfuric acid but some are done in alkaline electrolytes such alkali hydroxides, alkoxides or solutions of salts like tetramethylammonium chloride in methanol [128] or lithium chloride in alkyl amines [729,130]. 

Attempts to prepare a bicyclobutane by reductive cydization of cyclobutane-1,3-diones have been unsuccessful [114]. a,o)-Dibenzoylalkanes are reduced at a mercury cathode to cycloalkanediols only when a ring size of 5 or 6 results. These reactions have been achieved using either aqueous ethanolic sodium hydroxide [115] or acetonitrile containing tetramethylammonium tetrafluoroborate [113] as electrolyte. Attempts to extend the process to formation of 7-membered rings lead only to oligomeric materials. 

Electrohjsis/tetramethglammonium chloride Electrolytic reductions with tetramethylammonium Sulfinic acids and hydrocarbons from sulfones... 

Allyl p-tolyl sulfone and tetramethylammonium chloride in methanol cooled to 5°, then electrolyzed with a Hg-cathode and water as anolyte at 18-24 V and 1 amp. until after 30-35 min. vigorous Hg-evolution indicates completion of the reaction p-toluenesulfinic acid (Y 80%) and propylene (Y 75%). F. e. s. L. Horner and H. Neumann, B. 98, 1715 (1965) also selective removal of protective groups from peptides s. B. 98, 3462 (1965) with tetramethylammonium tosylate, ring closures by intramolecular electrolytic reduction of activated dienes s. J. D. Anderson and M. M. Baizer, Tetrah. Let. 1966, 511. 

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