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An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O.
The word "enamine" is apparently derived from the prefix en-, used as the suffix of alkene, and the root amine. Compare with enol, which is a molecule containing both alkene (en-) and alcohol (-ol).
If one of the nitrogen substituents is H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautormerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom.
Form
R2C = CR − NR2
See also
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- This page was last modified on 23 September 2008, at 00:05.
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