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Electrochemical Reduction Of Alkyl Halides At Vitreous Carbon Cathodes In Dimethylformamide, James Cleary, Mohammed Mubarak, Kenneth Viera, Mark Anderson, Dennis Peters
Electrochemical Reduction Of Alkyl Halides At Vitreous Carbon Cathodes In Dimethylformamide, James Cleary, Mohammed Mubarak, Kenneth Viera, Mark Anderson, Dennis Peters
Mark R. Anderson
At vitreous carbon electrodes in dimethylformamide which contains tetramethylammonium perchlorate, cyclic voltammograms for 1-iododecane, 1-bromodecane, and 2-bromooctane consist of one irreversible reduction wave signaling formation of the alkyl carbanion, whereas voltammograms for 2-iodooctane, t-butyl bromide, and t-butyl iodide reveal stepwise generation of the alkyl radical and carbanion. Large-scale electrolysis of 1-iododecane at reticulated vitreous carbon yields decane, eicosane, 1-decene, and 1-decanol; the first two compounds arise, respectively, from reaction of decyl carbanions with a proton donor and with unreduced alkyl iodide, whereas the last two species are produced via chemical attack of hydroxide ion on 1-iododecane. Reduction of 1-bromodecane results …
Electrochemistry Of 1,1,4,4-Tetraphenyl-1,3-Butadiene, 1,1,4,4-Tetraphenyl-1,2-Butadiene, And 1,1,4,4-Tetraphenyl-1-Butene In Dimethylformamide, Tsu-Yu Chen, Mark Anderson, Dennis Peters
Electrochemistry Of 1,1,4,4-Tetraphenyl-1,3-Butadiene, 1,1,4,4-Tetraphenyl-1,2-Butadiene, And 1,1,4,4-Tetraphenyl-1-Butene In Dimethylformamide, Tsu-Yu Chen, Mark Anderson, Dennis Peters
Mark R. Anderson
In dimethylformamide containing tetra-n-butylammonium perchlorate, 1,1,4,4-tetraphenyl-1-butene exhibits a single polarographic wave; preparative-scale reduction of the starting material produces 1,1,4,4-tetraphenylbutane.A polarogram for 1,1,4,4-tetraphenyl-1,3-butadiene consists of three waves. Large-scale electrolysis of 1,1,4,4-tetraphenyl-1,3-butadiene at potentials corresponding to either the first or second wave yields 1,1,4,4-tetraphenyl-1-butene in the absence of a proton donor and a mixture of 1,1,4,4-tetraphenyl-2-butene and 1,1,4,4-tetraphenyl-1-butene in the presence of excess glacial acetic acid. If 1,1,4,4-tetraphenyl-1,3-butadiene is electrolyzed at a potential on the third polarographic wave, one obtains 1,1,4,4-tetraphenylbutane in the absence of a proton donor but a mixture of 1,1,4,4-tetraphenyl-2-butene and 1,1,4,4-tetraphenylbutane in the presence of glacial acetic acid. …