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Amine alkylation (amino-dehalogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. [1] The reaction is called nucleophilic aliphatic substitution (of the halide), and the reaction product is a higher substituted amine. The method is widely used in the laboratory, but less so industrially, where alcohols are ...
The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. [1] [2] [3] The reaction is named after the German chemist Siegmund Gabriel. [4] The Gabriel reaction has been generalized to include the alkylation of sulfonamides [5] and imides ...
Conversion of the primary amine to an imine (Schiff base) using an aldehyde. [3] Alkylation of the imine using an alkyl halide, forming an iminium ion. [4] Hydrolysis of the iminium, releasing the secondary amine and regenerating the aldehyde. [5] Because the actual alkylation occurs on the imine, over-alkylation is not possible.
Quaternary ammonium compounds are prepared by the alkylation of tertiary amine. Industrial production of commodity quat salts usually involves hydrogenation of fatty nitriles, which can generate primary or secondary amines. These amines are then treated with methyl chloride. [4] The quaternization of alkyl amines by alkyl halides is widely ...
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 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 Stork enamine reaction. The reaction also applies to acyl halides as electrophiles, which results in the formation of 1,3-diketones (Stork acylation). [2] It is also effective for activated sp 3 alkyl electrophiles, including benzylic, allylic/propargylic, α-carbonyl (e.g., bromoacetone), and α-alkoxy (e.g., methoxymethyl chloride) alkyl ...
Aside from their basicity, the dominant reactivity of amines is their nucleophilicity. [16] Most primary amines are good ligands for metal ions to give coordination complexes. Amines are alkylated by alkyl halides. Acyl chlorides and acid anhydrides react with primary and secondary amines to form amides (the "Schotten–Baumann reaction ...