Amide—>-hydride exchange

The carbonyl intermediate then reacts readily with a primary amine to afford an imine and water. A subsequent addition of the iridium hydride to the C=N double bond of the imine, followed by amide-alkoxide exchange, would then occur to release the product. 

A number of basic materials such as hydroxides, hydrides and amides of alkaline and alkaline earth metals and metal oxides such as zinc oxide and antimony oxide are useful catalysts for the reaction. Acid ester-exchange catalysts such as boric acid, p-toluene sulphonic acid and zinc chloride are less... 

The heterocycles react directly with alkali metals or undergo exchange reactions with, for example, sodium amide and hydride, n-butyllithium and thallium ethoxide, to form the TV-heteroaryl salts. The salts of the alkali metals exist as solvent separated ion-pairs or as contact ion-pairs (71JOC3091), as do the quaternary ammonium salts, whereas the salts of the heavier metals are generally considered to have a high N—metal covalent character. These characteristics, which can be modified by a change in the polarity of the solvent, control the reactions of the heteroaryl anions. 

Cyclization of to-halocarboxamides (equation 46) requires the use of metallic amides and hydrides under anhydrous conditions. Phase transfer catalysis with strongly basic ion exchange resins in 50% sodium hydroxide solution give four- to seven-membered lactams in good to excellent yield. ... 

Color reactions Boric acid (hydroxyquinones). Dimethylaminobenzaldehyde (pyrroles). Ferric chloride (enols, phenols). Haloform test. Phenylhydrazine (Porter-Silber reaction). Sulfoacetic acid (Liebermann-Burchard test). Tetranitromethane (unsaturation). Condensation catalysts /3-Alanine. Ammonium acetate (formate). Ammonium nitrate. Benzyltrimethylammonium chloride. Boric acid. Boron trilluoride. Calcium hydride. Cesium fluoride. Glycine. Ion-exchange resins. Lead oxide. Lithium amide. Mercuric cyanide. 3-Methyl-l-ethyl-2-phosphoiene-l-oxlde. 3-Methyl-1-phenyi-3-phoipholene-1-oxide. Oxalic acid. Perchloric acid. Piperidine. Potaiaium r-butoxIde. Potassium fluoride. Potassium... 

Dehydrohalogenation Benzyltrimethylammonium mcsitoate. r-Butylamine. Calcium carbonate. j Uidine. Diazabicyclo[3.4.0]nonene-5. N.N-Dimethylaniline (see also Ethoxy-acetylene, preparation). N,N-Dimelhylformamide. Dimethyl sulfoxide-Potassium r-but-oxide. Dimethyl sulfoxide-Sodium bicarbonate. 2,4-Dinitrophenylhydrazine. Ethoxy-carbonylhydrazine. Ethyldicyclohexylamine. Ethyidiisopropylamine. Ion-exchange resins. Lithium. Lithium carbonate. Lithium carbonate-Lithium bromide. Lithium chloride. Methanolic KOH (see DimethylTormamide). N-PhenylmorphoKne. Potassium amide. Potassium r-butoxide. Pyridine. Quinoline. Rhodium-Alumina. Silver oxide. Sodium acetate-Acetonitrile (see Tetrachlorocyclopentadienone, preparation). Sodium amide. Sodium 2-butylcyclohexoxide. Sodium ethoxide (see l-Ethoxybutene-l-yne-3, preparation). Sodium hydride. Sodium iodide in 1,2-dimethoxyethane (see Tetrachlorocyclopentadienone, alternative preparation) Tetraethylammonium chloride. Tri-n-butylamine. Triethylamine. Tri-methyiamine (see Boron trichloride). Trimethyl phosphite. 

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