Electrochemical reduction of Phenylacetyl chloride (cas 103-80-0) and hydrocinnamoyl chloride at mercury cathodes in acetonitrile

Add time:08/12/2019    Source:sciencedirect.com

Cyclic voltammograms for the reduction of Phenylacetyl chloride (cas 103-80-0) and hydrocinnamoyl chloride at mercury cathodes in acetonitrile containing tetraalkylammonium perchlorates exhibit two waves. For each compound the first wave is attributable to cleavage of the carbon-chlorine bond, whereas the second wave is caused by the combined reductions of the respective aldehyde and acid anhydride—phenylacetaldehyde and phenylacetic anhydride (from phenylacetyl chloride), and hydrocinnamaldehyde and hydrocinnamic anhydride (from hydrocinnamoyl chloride). Controlled-potential electrolyses of phenylacetyl chloride yield 1,4-diphenyl-2-butene-2,3-diol diphenylacetate, phenylacetaldehyde, 1,3-diphenylacetone and toluene; phenylacetic anhydride and phenylacetic acid are chemically formed byproducts. Electrolyses of hydrocinnamoyl chloride produce 1,6-diphenyl-3-hexene-3,4-diol dihydrocinnamate, hydrocinnamaldehyde and ethylbenzene; hydrocinnamic anhydride and hydrocinnamic acid result from chemical reactions of the starting material with water. Using acetonitrile-d3 and deuterium oxide, we have determined that phenylacetaldehyde and hydrocinnamaldehyde are formed from both acyl radical and anion intermediates. Under comparable conditions, the yield of hydrocinnamaldehyde is higher than that of phenylacetaldehyde, mainly because the hydrocinnamoyl radical decarbonylates more slowly than the phenylacetyl radical. In addition, the production of phenylacetaldehyde and hydrocinnamaldehyde is influenced by the tetraalkylammonium cation that comprises the supporting electrolyte.

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