Acylation nitriles

Using an Aldehydo Amide, Nitrile, Acyl Halide, or Related Synthon... 

Acid derivatives that can be converted to amides include thiol acids (RCOSH), thiol esters (RCOSR), ° acyloxyboranes [RCOB(OR )2]. silicic esters [(RCOO)4Si], 1,1,1-trihalo ketones (RCOCXa), a-keto nitriles, acyl azides, and non-enolizable ketones (see the Haller-Bauer reaction 12-31). A polymer-bound acyl derivative was converted to an amide using tributylvinyl tin, trifluoroacetic acid, AsPh3, and a palladium catalyst. The source of amine in this reaction was the polymer itself, which was an amide resin. 

Acid derivatives that can be converted to amides include thiol acids RCOSH, thiol esters RCOSR,911 acyloxyboranes RCOB(OR )2,912 silicic esters (RCOO)4Si, 1,1,1-trihalo ketones RCOCX3,913 a-keto nitriles, acyl azides, and nonenolizable ketones (see the Haller-Bauer reaction 2-33). 

In the benzoin condensation, one molecule of aldehyde serves as an electrophile. If a carbanion is generated from protected cyanohydrins, a-aminonitriles or dithioacetals, it can react with electrophiles such as alkyl halides, strongly activated aryl halides or alkyl tosylates to form ketones. Amongst other electrophiles which are attacked by the above carbanions are heterocyclic A -oxides, carbonyl compounds, a,p-unsaturated carbonyl compounds, a,3-unsaturated nitriles, acyl halides, Mannich bases, epoxides and chlorotiimethyl derivatives of silicon, germanium and tin. 

Esters Carboxylic acids Nitriles Ketones Amides Esters Nitriles Acyl chlorides Acid anhydrides Acyl cyanides Carbon dioxide Alkyl dialkoxyphosphinyl formate A l imidazoles Thiol esters Thio esters... 

IV. Ammoniiun salts of carboxylic adds, aldehyde-ammonias, amides, imides, nitriles. Acyl derivatives of bases (JV-substituted amides). Hydrazines, semicarbazide, hydroxyl-amine, their salts and carbonyl derivatives. Condensation products of aldehydes with ammonia or amines. 

Ammonium Salts of Carboxylic Adds Aldehyde-ananomas Anodes Inodes Nitriles Acyl Derivatives of Bases Hydrazines, Sendcarbazide, Hydroxylandne, their salts and carbonyl derivatives Condensation Products of Aldehydes with Amntonia or Andnes... 

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