Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Reductive Coupling Reactions of Benzyl Chloride by Copper(I) Complexes
Keisuke WadaHarukichi Hashimoto
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1968 Volume 41 Issue 12 Pages 3001-3007

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Abstract

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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