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Reformatsky reaction
The Reformatsky reaction (sometimes spelled Reformatskii reaction) is an organic reaction which condenses aldehydes (or ketones),, with α-halo esters, , using a metallic zinc to form β-hydroxy-esters:
The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates or Grignard reagents and hence nucleophilic addition to the ester group does not occur. The reaction was discovered by Sergey Nikolaevich Reformatsky.
Some reviews have been published.
== Structure of the reagent ==
The crystal structures of the THF complexes of the Reformatsky reagents ''tert''-butyl bromozincacetate and ethyl bromozincacetate have been determined. Both form cyclic eight-membered dimers in the solid state, but differ in stereochemistry: the eight-membered ring in the ethyl derivative adopts a tub-shaped conformation and has ''cis'' bromo groups and ''cis'' THF ligands, whereas in the ''tert''-butyl derivative, the ring is in a chair form and the bromo groups and THF ligands are ''trans''.
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