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The mechanism of the Mannich reaction starts with the formation of an iminium ion from the amine and formaldehyde. [4]: 140 The compound with the carbonyl functional group (in this case a ketone) will tautomerize to the enol form, after which it attacks the iminium ion.
The Eschweiler–Clarke reaction (also called the Eschweiler–Clarke methylation) is a chemical reaction whereby a primary (or secondary) amine is methylated using excess formic acid and formaldehyde. [1] [2] Reductive amination reactions such as this one will not produce quaternary ammonium salts, but instead will stop at the tertiary amine ...
The Delépine reaction is the organic synthesis of primary amines (4) by reaction of benzyl or alkyl halides (1) with hexamethylenetetramine (2) followed by acid hydrolysis of the quaternary ammonium salt (3). [1] [2] It is named after the French chemist Stéphane Marcel Delépine (1871–1965). Delepin reaction
In this method, the sodium or potassium salt of phthalimide is N-alkylated with a primary alkyl halide to give the corresponding N-alkylphthalimide. [8] [9] [10] Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. [11] Alternatively the workup may be via the Ing–Manske procedure, involving reaction with hydrazine.
The reaction mechanism of the Stevens rearrangement is one of the most controversial reaction mechanisms in organic chemistry. [4] Key in the reaction mechanism [5] [6] for the Stevens rearrangement (explained for the nitrogen reaction) is the formation of an ylide after deprotonation of the ammonium salt by a strong base.
A Mannich base is a beta-amino-ketone, which is formed in the reaction of an amine, formaldehyde (or an aldehyde) and a carbon acid. [1] The Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of a non-enolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine (iminium ion or imine salt).
The first reaction is the formation of the N-2,4-dinitrophenyl-pyridinium salt (2). This salt is typically isolated and purified by recrystallization. The formation of the DNP-pyridinium salt. Upon heating a primary amine with the N-2,4-dinitrophenyl-pyridinium salt (2), the addition
The vast majority of these procedures utilize the commercially available salt N,O-dimethylhydroxylamine hydrochloride [MeO(Me)NH•HCl], which is typically easier to handle than the free amine. [6] Treatment of an ester or lactone with AlMe 3 or AlMe 2 Cl affords the corresponding Weinreb amide in good yields. Alternatively, non-nucleophilic ...