Abstract
In the presence of electrogenerated nickel(I) salen in acetonitrile containing tetramethylammonium tetrafluoroborate, cyclohexanecarbonyl chloride is catalytically reduced to form ultimately a tetrameric species, 1,2-dicyclohexylethene-1,2-diol dicyclohexanoate. Initially, the acyl chloride accepts an electron from nickel(I) salen to form an acyl radical, and two acyl radicals couple to afford 1,2-dicyclohexylethane-1,2-dione. As soon as it is formed, the latter α-diketone undergoes either direct (noncatalytic) or nickel(I) salen-catalyzed reduction to its radical-anion, which can attack unreduced cyclohexanecarbonyl chloride; the resulting intermediate is further reduced and acylated to produce the tetramer.
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