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In chemistry, the hydrogenation of carbon–nitrogen double bonds is the addition of the elements of dihydrogen (H 2) across a carbon–nitrogen double bond, forming amines or amine derivatives. [1] Although a variety of general methods have been developed for the enantioselective hydrogenation of ketones, [ 2 ] methods for the hydrogenation of ...
[4] The same is true when an alkene reacts with water in an additional reaction to form an alcohol that involves carbocation formation. The hydroxyl group (OH) bonds to the carbon that has the greater number of carbon-carbon bonds, while the hydrogen bonds to the carbon on the other end of the double bond, that has more carbon–hydrogen bonds.
Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts: [4] C 6 H 5 NH 2 + 3 H 2 → C 6 H 11 NH 2 It is also prepared by alkylation of ammonia using cyclohexanol .
Steps in the hydrogenation of a C=C double bond at a catalyst surface, for example Ni or Pt : (1) The reactants are adsorbed on the catalyst surface and H 2 dissociates. (2) An H atom bonds to one C atom. The other C atom is still attached to the surface. (3) A second C atom bonds to an H atom. The molecule leaves the surface.
2 R-C≡N + 4 H 2 → (R-CH 2) 2 NH + NH 3 3 R-C≡N + 6 H 2 → (R-CH 2) 3 N + 2 NH 3. Such reactions proceed via enamine intermediates. [8] The most important reaction condition for selective primary amine production is catalyst choice. [1] Other important factors include solvent choice, solution pH, steric effects, temperature, and the ...
The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material. [4]
For example, in the three-component coupling of aldehydes, amines, and activated alkenes, the aldehyde reacts with the amine to produce an imine prior to forming the aza-MBH adduct, as in the reaction of aryl aldehydes, diphenylphosphinamide, and methyl vinyl ketone, in the presence of TiCl 4, triphenylphosphine, and triethylamine: [19]
2-Aminoalcohols are an important class of organic compounds that are often generated by the reaction of amines with epoxides: C 2 H 4 O + R−NH 2 → RNHC 2 H 4 OH. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases. [2] Hydrogenation or hydride reduction of amino acids gives the