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The general structure of an enamine. An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. [1] [2] Enamines are versatile intermediates. [3] [4] Condensation to give an enamine. [5] The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine.
When R = H, the compound is a primary imine, when R is hydrocarbyl, the compound is a secondary imine. If this group is not a hydrogen atom, then the compound can sometimes be referred to as a Schiff base. [9] When R 3 is OH, the imine is called an oxime, and when R 3 is NH 2 the imine is called a hydrazone.
A general linear imide functional group. In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. [1] The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis.
The reduction of oximes by sodium metal, [10] sodium amalgam, hydrogenation, or reaction with hydride reagents produces amines. [11] Typically the reduction of aldoximes gives both primary amines and secondary amines; however, reaction conditions can be altered (such as the addition of potassium hydroxide in a 1/30 molar ratio) to yield solely ...
enamine – imine: H−N−C=C ⇌ N=C−C−H. cyanamide – carbodiimide; guanidine – guanidine – guanidine: With a central carbon surrounded by three nitrogens, a guanidine group allows this transform in three possible orientations
General structure of an imine. Schiff bases are imines in which R 3 is an alkyl or aryl group (not a hydrogen). R 1 and R 2 may be hydrogens General structure of an azomethine compound. In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure R 1 R 2 C=NR 3 (R 3 = alkyl or aryl, but not hydrogen).
The C=N bonds, which are near 129 picometers in length, are shorter than C-N single bonds. Cis/trans isomers are observed. The C=N distance is slightly shorter in iminium cations than in the parent imine, and computational studies indicate that the C=N bonding is also stronger in iminium vs imine, although the C=N distance contracts only slightly.
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.