Balz Schiemann Reaction Mechanism

Balz Schiemann Reaction

• The Balz–Schiemann reaction is an organic reaction involving the rearrangement of an aryl ketone to an aryl ester. The reaction is named for Wilhelm Balz and Hermann Schiemann, who first reported it in 1901.
• The Balz–Schiemann reaction proceeds through an aryl migration step, in which the aryl group migrates from the ketone to the ester. The mechanism of the reaction is thought to involve an initial addition of the ketone to the ester, followed by a second addition of the aryl group. This second addition is thought to occur through a carbocation intermediate, which is then stabilized by resonance.

Balz Schiemann Reaction and Its Mechanisms

• The Balz Schiemann reaction is a chemical reaction between an alcohol and a Grignard reagent to form an alkyl magnesium halide. The reaction is named for the German chemist Balz Schiemann, who first reported it in 1894.
• The mechanism of the Balz Schiemann reaction is the formation of a carbon-carbon bond between the alcohol and the Grignard reagent. The carbon-carbon bond is formed by the elimination of a hydrogen atom from the alcohol, and the formation of a magnesium halide.

What is Diazotization?

Diazotization is a chemical reaction between an amine and nitrous acid, producing a diazonium salt. The diazonium salt is a white crystalline solid that is soluble in water.

Schiemann Reaction Development Over The Years

• The Schiemann Reaction is a synthetic organic reaction that produces an α,β-unsaturated ketone from an α,β-unsaturated aldehyde and an organolithium reagent. The reaction was first reported by Georg Schiemann in 1894.
• The Schiemann Reaction has been used extensively in the synthesis of pharmaceuticals and natural products. The reaction is typically performed using a Grignard reagent or organolithium reagent as the nucleophile. The most common organolithium reagent used in the Schiemann Reaction is n-butyllithium.
• The Schiemann Reaction can be performed using a variety of aldehydes and ketones. The most common substrates are alkenes and alkynes. The reaction is typically performed in the presence of a base, such as potassium carbonate or potassium tert-butoxide. The reaction is typically carried out in anhydrous conditions.
• The Schiemann Reaction is a very efficient reaction and typically produces good yields of the desired product. The reaction is also very fast, typically completing in less than one hour.