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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.
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 relationship of imines to amines having double and single bonds can be correlated with imides and amides, as in succinimide vs acetamide. Imines are related to ketones and aldehydes by replacement of the oxygen with an NR group. When R = H, the compound is a primary imine, when R is hydrocarbyl, the compound is a
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.
or when an α-carbonyl proton is present to an enamine: In acidic environment the reaction product is an iminium salt by loss of water. This reaction type is found in many Heterocycle preparations for example the Povarov reaction and the Friedländer-synthesis to quinolines .
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Heating magnesium amide to about 400 °C yields magnesium imide with the loss of ammonia. Magnesium imide itself decomposes if heated between 455 and 490 °C. [6] Beryllium imide forms from beryllium amide when heated to 230 °C in a vacuum. [7] When strontium metal is heated with ammonia at 750 °C, the dark yellow strontium imide forms. [8]
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.