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Nick Brummel

Dehalogenation of vicinal dihalides

Dawood Khan  Follow

Zinc is used effectively in the dehalogention of vicinal dihalides because a carbon zinc complex is formed in the mechanism which is probably more stable. This reaction is also known as Simmon' Smith reaction.

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The stability and usefulness of the Simmons-Smith reagent (zinc metal)may be attributed in part to the higher covalency of the carbon-zincbond together with solvation and internal coordination of the zinc (which makes the zinc complex stable). (Source)

Reduction of vicinal dihalides by zinc metal proceeds by way ofoxidative insertion of Zn(0) into a C-X bond, producing an organozincspecies (stable) which undergoes dehalogenation:

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(source)

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Jakob Kr?mer  Follow
The Simmons-Smith reaction is the dehalogenation of a More
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Esther Etiekak  Follow
dihalide, and thus shouldn’t be the main point of interest here.More
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Jim Merrilees  Follow
geminalMore
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