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In recent years, several reagents such as Tris(2,2,2-trifluoroethyl)borate [B(OCH 2 CF 3) 3], [14] pyrrolidine [15] or titanium ethoxide [Ti(OEt) 4] [16] have been shown to catalyse imine formation. Rarer than primary amines is the use of ammonia to give a primary imine. [17] In the case of hexafluoroacetone, the hemiaminal intermediate can be ...
The reaction is generally performed in an aqueous solution at close to boiling. The first methylation of the amine begins with imine formation with formaldehyde. The formic acid acts as a source of hydride and reduces the imine to a secondary amine. Loss of carbon dioxide gas renders the reaction irreversible. Despite being more hindered, the ...
Reaction of cyclohexylamine with acetaldehyde forming an imine. Sodium sulfate removes water [1] In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. [2] The reaction name is based on the IUPAC Nomenclature for Transformations.
General structure of an imine. Schiff bases are imines in which R 3 is an alkyl or aryl group (not a hydrogen). R 1 and R 2 may be hydrogens General structure of an azomethine compound. In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure R 1 R 2 C=NR 3 (R 3 = alkyl or aryl, but not hydrogen).
First, the nickel metal dehydrogenates the alcohol to form a ketone and Ni-H complex. Then, the ketone reacts with ammonia to form an imine. Finally, the imine reacts with Ni-H to regenerate catalyst and form primary amine. An example of a homogeneous catalytic system is the reductive amination of ketones done with an iridium catalyst. [20]
An example of nitro group reduction to an amine using SnCl 2 and HCl was also disclosed by Duden and co-workers, thus representing the first use of the nitro-Mannich reaction to prepare polyamines. The next report did not appear until 1931, [ 9 ] when Cerf de Mauny conducted a thorough study of Henry’s original work using hemiaminals.
The initial product is a thioamide for example that of acetophenone [7] which can again be hydrolyzed to the amide. The reaction is named after Karl Kindler The Kindler modification of the Willgerodt rearrangement. A possible reaction mechanism for the Kindler variation is depicted below: [8]
Catalytic cycle for reduction of imine to an amine using an FLP. Reduction of imines, nitriles, and aziridines to primary and secondary amines traditionally is effected by metal hydride reagents, e.g. lithium aluminium hydride and sodium cyanoborohydride. Hydrogenations of these unsaturated substrates can be effected by metal-catalyzed reactions.