Organomercurials cathodes

The Hg cathode plays the role of a reducing catalyst. Electrochemical reduction of 8-bromoboman-2-one in an HMPA-Bu4NBr-(Pt/Hg) system also suggests the formation of an organomercurial intermediate that leads to the formation of dihydrocarvone as the major product [553]. 

Organomercury compounds can also be obtained in preparatively useful quantitites by the action of radicals on metallic mercury. For example, aryl-mercuric compounds are formed on decomposition of arenediazonium salts in the presence of metallic mercury 28 and when 3-iodopropionitrile is reduced electrolytically at a mercury cathode, the radicals produced react with the cathode material forming bis-(2-cyanoethyl)mercury.202 Organomercury compounds are also obtained analogously on reduction of ketones at a mercury cathode.203... 

The mechanism of the formation of oi anometallic compounds in cathodic processes is at present under discussion. On its own the fact of "cathodic dissolution of metal" is paradoxical. Tafel, who first observed the dissolution of mercury during electrolysis of acetone solutions, called this phenomenon the "peculiar formation" of organomercury compounds 6J. 

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