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In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides. Menshutkin-reaction. The reaction is the method of choice for the preparation of quaternary ammonium salts. [1]
The mechanism of the Eschweiler–Clark reaction. From this mechanism it is clear that a quaternary ammonium salt will never form, because it is impossible for a tertiary amine to form another imine or iminium ion. Chiral amines typically do not racemize under these conditions. [6]
The Forster–Decker method is a series of chemical reactions that have the effect of mono-alkylating a primary amine (1), forming a secondary amine (6). [1] [2] The process occurs by way of transient formation of an imine (3) that undergoes the actual alkylation reaction.
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.
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. This method produces a precipitate of phthalhydrazide (C 6 H 4 (CO) 2 N 2 H 2) along with the primary amine: C 6 H 4 (CO) 2 NR + N 2 H 4 → C 6 H 4 (CO) 2 N 2 ...
A second addition of amine leads to the displacement of 2,4-dinitroaniline (5) and formation of the König salt [5] (6a and 6b). The trans-cis-trans isomer of the König salt (6a) can react by either sigmatropic rearrangement or nucleophilic addition of a zwitterionic intermediate to give cyclized intermediate (7). [6] This has been suggested ...
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
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).