1968 Volume 41 Issue 12 Pages 3001-3007
The reactions between benzyl chloride and cuprous chloride were studied. It was found that good yields of bibenzyl were obtained by the addition of ethylenediamine, diethylenetriamine, triethylenetetramine, acetylacetone and EDTA. Nothing of bibenzyl was observed in the cases of ethanolamine, pyridine, dipyridyl, phenanthroline and triphenylphosphine. These facts, together with the spectral studies of copper complexes can reasonably be explained by the formation of reactive species of the type CuI(en)nCl. The course of the reaction was discussed on the basis of the substituent and medium effects. Radical but not free type mechanisms which include the transient organocopper species were considered. Some additional comments were also made.
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