Abstract
Cyclic voltammetry and controlled-potential electrolysis have been employed to investigate the electrochemical behavior of 1,4-dibromo-, 1,4-diiodo-, 1-bromo-4-chloro- and 1-chloro-4-iodobutane at glassy carbon cathodes in dimethylformamide containing tetramethylammonium perchlorate. Depending on the identity of the 1,4-dihalobutane electrolyzed and the choice of potential, reduction of these compounds leads to a myriad of products including cyclobutane, n-butane, n-octane, 1-butene, cis -and trans -2-butene, 1,3-butadiene, ethylene, 1-chlorobutane, 1-bromobutane, 1-iodobutane, 1-iodooctane, 1,4-dichlorobutane, 1,8-dichlorooctane, and 1,8-diiodooctane. Experiments involving the use of proton donors (phenol and 1,1,1,3,3,3-hexafluoro-2-propanol), a radical trap (norbornylene), and several deuterium ion or atom donors have been utilized to elucidate the mechanisms by which the various electrolysis products are formed.
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