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KMID : 1059519930370020228
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Journal of the Korean Chemical Society
1993 Volume.37 No. 2 p.228 ~ p.236
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Effect of Transition Metal Ion on the Reaction of Benzylbromide with Grignard Reagent
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Kim Jack C.
Koh Young-Sim
Yoo Ung-Chan
Kim Min-Sook
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Abstract
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The effect of ferric ion on the reaction of CH3MgI with benzylbromide was investigated by determining the product ratio between cross-coupling product, ethylbenzene (A) and homocoupling product, bibenzyl (B) in the presence of ferric ion. When CH3MgI prepared with pure magnesium was used, the ratio of A to B was 22 to 78 and with reagent grade magnesium, the ratio became 33 to 67 indicating that metallic impurities in magnesium affect the reaction mechanism to lead less homocoupling product, B. The ratio changes became significant when ferric chloride was added in the reaction mixture in catalytic amounts and the ratio of A to B reached to 80 to 20 at maximum. The reaction in the presence of ferric ion seems to follow mainly an ionic mechanism which involves iron-benzyl bromide π-complex formation. The complex formation is expected to be able to enhance ionic attack of CH3MgI on benzyl carbon to give more A.
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