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Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group. [1] [2] ... Toggle the table of contents.
In a similar fashion, the intermediate isocyanate can be trapped by tert-butyl alcohol, yielding the tert-butoxycarbonyl (Boc)-protected amine. The Hofmann Rearrangement also can be used to yield carbamates from α,β-unsaturated or α-hydroxy amides [2] [8] or nitriles from α,β-acetylenic amides [2] [9] in good yields (≈70%).
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the ...
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 ...
The secondary amide 1 reacts via its enolized form with phosphorus pentachloride to form the oxonium ion 2. This produces a chloride ion which deprotonates the oxonium ion to form and imine 3 and hydrogen chloride. These then react with one another to form an amine, with loss of the phosphorus chloride residue.
Amide reduction: Amines, aldehydes Reagent: lithium aluminium hydride followed by hydrolysis Vilsmeier–Haack reaction: Aldehyde (via imine) POCl 3, aromatic substrate, formamide Bischler–Napieralski reaction: Cyclic aryl imine: POCl 3, SOCl 2, etc. Tautomeric chlorination: Imidoyl chloride: Oxophilic halogenating agents, e.g. COCl 2 or SOCl 2
These possibilities have been used to account for the fact that, for certain substrates like α-tetralone, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides. [8] Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction
Typically, the amine oxide is prepared from the corresponding amine with a peroxy acid or comparable oxidant. The actual elimination requires just heat. The actual elimination requires just heat. Illustrative is a synthesis of methylenecyclohexane : [ 5 ]