Reformatsky reaction

[3][4] In addition[5] to aldehydes and ketones, it has also been shown that the Reformatsky enolate is able to react with acid chlorides,[6] imines,[7] nitriles (see Blaise reaction), and nitrones.

[8] Moreover,[5] metals other than zinc have also been used, including magnesium,[9] iron,[10] cobalt,[11] nickel,[12] germanium,[13] cadmium,[14] indium,[15][16] barium,[17] and cerium.

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.

The oxygen on an aldehyde or ketone coordinates to the zinc to form the six-member chair like transition state 3.

A rearrangement occurs in which zinc switches to the aldehyde or ketone oxygen and a carbon-carbon bond is formed 4.