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The Rosenmund–von Braun synthesis is an organic reaction in which an 
aryl halide In organic chemistry, an aryl halide (also known as haloarene) is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhi ...
reacts with cuprous cyanide
Copper(I) cyanide is an inorganic compound with the formula CuCN. This off-white solid occurs in two polymorphs; impure samples can be green due to the presence of Cu(II) impurities. The compound is useful as a catalyst, in electroplating copper ...
to yield an aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromaticity, aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar ...
nitrile.
:
The reaction was named after Karl Wilhelm Rosenmund
Karl Wilhelm Louis Rosenmund (15 December 1884 – 8 February 1965) was a German chemist. He was born in Berlin and died in Kiel.
Rosenmund studied chemistry and received his Ph.D. 1906 from University of Berlin for his work with Otto Diels. He ...
who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of potassium cyanide and catalytic amounts of cuprous cyanide
Copper(I) cyanide is an inorganic compound with the formula CuCN. This off-white solid occurs in two polymorphs; impure samples can be green due to the presence of Cu(II) impurities. The compound is useful as a catalyst, in electroplating copper ...
at 200 °C. The reaction yields the carboxylic acid, not the nitrile, but Rosenmund speculated that the intermediate should be the nitrile. Independently Alfred Pongratz and improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction. Further improvement of the reaction was done in the following years, for example the use of ionic liquid
An ionic liquid (IL) is a salt in the liquid state. In some contexts, the term has been restricted to salts whose melting point is below a specific temperature, such as . While ordinary liquids such as water and gasoline are predominantly made of ...
s as solvent for the reaction.
See also
* Kolbe nitrile synthesis a similar reaction for the synthesis of alkyl nitrile *Sandmeyer reaction
The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts.
It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provide ...
*Von Braun reaction
The von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide.
An example is the reaction of ''N'',''N''-dimethyl-1-naphthylamine:
These days, most chemist have replaced cyanogen ...
References
{{DEFAULTSORT:Rosenmund-von Braun reaction Substitution reactions Name reactions