These reagents activate the acyl chloride via a nucleophilic catalysis mechanism. The amine attacks the carbonyl bond and presumably first forms a transient tetrahedral intermediate, then forms a quaternary acylammonium salt by the displacement of the leaving group. This quaternary acylammonium salt is more susceptible to attack by alcohols or other nucleophiles.

:::

The use of two phases (aqueous for amine, organic for acyl chloride) is called the Schotten-Baumann reaction.

1.Previous
3.Next