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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]
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 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]
Amine. In chemistry, amines (/ ə ˈ m iː n, ˈ æ m iː n /, [1] [2] UK also / ˈ eɪ m iː n / [3]) are compounds and functional groups that contain a basic nitrogen atom with a lone pair.Formally, amines are derivatives of ammonia (NH 3 (in which the bond angle between the nitrogen and hydrogen is 170°), wherein one or more hydrogen atoms have been replaced by a substituent such as an ...
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 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 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).