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The mechanism for the reduction of a nitrile to an aldehyde with DIBAL-H. The hydride reagent Diisobutylaluminium hydride, or DIBAL-H, is commonly used to convert nitriles to the aldehyde. [14] Regarding the proposed mechanism, DIBAL forms a Lewis acid-base adduct with the nitrile by formation of an N-Al bond. The hydride is then transferred to ...
Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE / MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin (II) chloride (SnCl 2), hydrochloric acid (HCl) and quenching the resulting iminium salt ( [R-CH=NH 2] + Cl −) with water (H 2 O). [1][2] During the ...
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.
The Béchamp reduction (or Béchamp process) is a chemical reaction that converts aromatic nitro compounds to their corresponding anilines using iron as the reductant: [ 1 ] 4 C6H5NO2 + 9 Fe + 4 H2O → 4 C6H5NH2 + 3 Fe3O4. This reaction was once a major route to aniline, but catalytic hydrogenation is the preferred method.
Nitrile hydratase and amidase are two hydrating and hydrolytic enzymes responsible for the sequential metabolism of nitriles in bacteria that are capable of utilising nitriles as their sole source of nitrogen and carbon, and in concert act as an alternative to nitrilase activity, which performs nitrile hydrolysis without formation of an intermediate primary amide.
Henry reaction. The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-nitro alcohols. [1][2][3] This type of reaction is also referred ...
Pinner reaction. The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt. [1] The reaction is named after Adolf Pinner, who first described it in 1877. [2][3][4] Pinner salts are themselves reactive and undergo ...
Cyanohydrin. The structure of a general cyanohydrin. In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C (OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors ...