Add time:08/03/2019         Source:sciencedirect.com

In dimethylformamide containing tetramethylammonium perchlorate, reduction of 1,10-diiododecane yields two irreversible voltammetric waves at mercury, whereas reduction of 1,10-dibromodecane gives only one irreversible wave. Quantitative comparison of this behavior with that known for 1-iodo- and 1-bromodecane suggests that 1,10-diiododecane is reduced in a pair of two-electron steps and that 1,10-dibromodecane undergoes a single four-electron reduction. Preparative-scale electrolyses of 1,10-di-iododecane at a potential on its first reduction wave reveal that an organomercury polymer is the only product. At potentials corresponding to the second wave for 1,10-diiododecane and to the first wave for 1,10-dibromodecane, the electrolysis products include decane, 1-decene, 1,9-decadiene, 1-decanol, and 9-decen-1-ol along with telomers formed by attack of solvent-derived radicals on either 1-decene or 1,9-decadiene. When electrolyses of 1,10-diiodo- and 1,10-dibromodecane are performed in the presence of a proton donor (diethyl malonate), the yield of decane increases, but no alcohols or unsaturated compounds are formed; instead, products such as diethyl n-decylmalonate and diethyl n-eicosylmalonate are found which arise from attack of the diethyl malonate anion on unreduced starting material.

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