Electroorganic Chemistry. VII. The Role of Mercuric Salts in the Electroreduction of Benzylic Bromides

Electroduction of a variety of benzylic mono- and 1,3-dibromides and of benzylmer curie halides at stirred mercury pool cathode leads to products that support a mechanism for the electro- duction of bromides that involves organomercury(I) intermediates and perhaps mercury (I) dimers. Products f ormed in the presence or absence of strongly adsorbed but eleotrochemically indifferent species suggest that monomolecular versus bimolecular reactions of the adsorbed organomercury(I) intermediates or dimers are strongly influenced by the presence of such species and that in some cases the reaction can be directed to one or another final product, providing a measure of control in synthetic applications

Electroorganic Chemistry. VI. Mechanism and Product Studies in the Electroreductoin of 1,3-Dibromides

Products of the electroreduction of 1,3-dihromopropane, 1, 3-dibromo-1 -phenylpropane, 1,3-dibromo-1,3 -diphenylpropane, enđo-4-syn-8-dibromodibenzobicyclo[3.2.1] octadiene, and 1,8-bis- (bromomethyl)naphthalene at a mercury cathode were examined. The influence of change in potential, of addition of radical and carbanion scavengers, of added adsorbable species on product distribution, and the presence of organomercurial species in the products implicate a reaction path which involves sequential one electron reductions with the intervention of organomercury(l) radicals and possible dimeric mercury(l) species