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The Letts nitrile synthesis is a chemical reaction of aromatic carboxylic acids with metal thiocyanates to form nitriles. The reaction includes the loss of carbon dioxide and potassium hydrosulfide. The polar basic substitution reaction was discovered in 1872 by Edmund A. Letts. [1] [2] The Letts nitrile synthesis
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
The Rosenmund–von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to yield an aryl nitrile. [1] [2] [3]The reaction was named after Karl Wilhelm Rosenmund 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 at 200 °C.
Nitrilase was first discovered in the early 1960s for its ability to catalyze the hydration of a nitrile to a carboxylic acid. [2] Although it was known at the time that nitrilase could operate with wide substrate specificity in producing the corresponding acid, later studies reported the first NHase (nitrile hydratase) activity exhibited by nitrilase.
With nitrile electrophiles, nucleophilic addition take place by: [1] hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction.
The reaction generates a nitrile and a carbocation, which is quickly intercepted to form a variety of products. The nitrile can also be hydrolyzed under reaction conditions to give carboxylic acids. Different reaction conditions can favor the fragmentation over the rearrangement.
Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst: [1] RR’C=O + HCN → RR’C(OH)CN
Hydrocyanation is important due to the versatility of alkyl nitriles (RCN), which are important intermediates for the syntheses of amides, amines, carboxylic acids and esters. Naproxen , an anti-inflammatory drug, is prepared via an asymmetric hydrocyanation of a vinylnaphthalene utilizing a phosphinite ( OPR 2 ) ligand, L .