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Effect of Transition Metal Ion on the Reaction of Benzylbromide with Grignard Reagent
Effect of Transition Metal Ion on the Reaction of Benzylbromide with Grignard Reagent
Kim, Jack C.;Koh, Young-Sim;Yoon, Ung-Chan;Kim, Min-Sook
Journal of the Korean Chemical Society. 1993. Feb, 37(2): 228-236
DOI : http://dx.doi.org/
  • Published : February 20, 1993
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Kim, Jack C.
Koh, Young-Sim
Yoon, Ung-Chan
Kim, Min-Sook
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Kim, Jack C.
Koh, Young-Sim
Yoon, Ung-Chan
Kim, Min-Sook
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Abstract
The effect of ferric ion on the reaction of CH_3$MgI with benzylbromide was investigated by determining the product ratio between cross-coupling product, ethylbenzene (A) and homocoupling product, bibenzyl (B) in the presence of ferric ion. When CH_3$MgI 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 ${\pi}$-complex formation. The complex formation is expected to be able to enhance ionic attack of CH_3$MgI on benzyl carbon to give more A.
Citing 'Effect of Transition Metal Ion on the Reaction of Benzylbromide with Grignard Reagent '
@article{ JCGMDC_1993_v37n2_228} ,title={Effect of Transition Metal Ion on the Reaction of Benzylbromide with Grignard Reagent} ,volume={2} , number= {2} , journal={Journal of the Korean Chemical Society} , publisher={Korean Chemical Society} , author={Jack C., Kim and Young-Sim, Koh and Ung-Chan, Yoon and Min-Sook, Kim} , year={1993} , month={Feb}