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A primary imine in which C is attached to both a hydrocarbyl and a H (derived from an aldehyde) is called a primary aldimine; a secondary imine with such groups is called a secondary aldimine. [10] A primary imine in which C is attached to two hydrocarbyls (derived from a ketone) is called a primary ketimine; a secondary imine with such groups ...
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).
The Schiff base is an electrophile which reacts in a second step in an electrophilic addition with an enol formed from a carbonyl compound containing an acidic alpha-proton. The Mannich reaction is a condensation reaction. [4]: 140 In the Mannich reaction, primary or secondary amines or ammonia react with formaldehyde to form a Schiff base ...
The Staudinger synthesis, also called the Staudinger ketene-imine cycloaddition, is a chemical synthesis in which an imine 1 reacts with a ketene 2 through a non-photochemical 2+2 cycloaddition to produce a β-lactam 3. [1] The reaction carries particular importance in the synthesis of β-lactam antibiotics. [2]
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]
Relevant to the inner sphere mechanism are the two modes by which imines can coordinate, as a π or as a σ-donor ligand. The pi-imines are also susceptible to conversion to iminium ligands upon N-protonation. The binding mode for the imine is unclear, both η 1 (σ-type) and η 2 (π-type). The final step in the mechanism is release of the ...
If one or both of the nitrogen substituents is a hydrogen atom it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location ...
Ethanimine is an organonitrogen compound classified as an imine. It is formed by reacting acetaldehyde and ammonia, but rapidly polymerizes to acetaldehyde ammonia trimer. It has two tautomers: ethanimine, an imine, and ethenamine or aminoethylene, an amine. Ethanimine has two hydrogens on the carbon, while ethenamine has two on the nitrogen atom.