Enamine

Enamine

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

R_2C=CR-NR_2

ee also

*Thorpe reaction


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  • Enamine — Énamine Structure générale d une énamine. Une énamine est un composé organique insaturé (alcène) obtenu par la réaction entre un aldéhyde ou une cétone et une amine secondaire, suivie d une libération de H2O. Si l un des substituants de l azote… …   Wikipédia en Français

  • Énamine — Structure générale d une énamine. Une énamine est un composé organique insaturé (alcène) obtenu par la réaction entre un aldéhyde ou une cétone et une amine secondaire, suivie d une libération de H2O. Si l un des substituants de l azote est H, c… …   Wikipédia en Français

  • Enamine — Allgemeiner Aufbau eines Enamins mit den Resten R1 bis R5, die Wasserstoffatome oder Organyl Reste (Alkyl Reste, Aryl Reste, Alkylaryl Reste etc.) sind. Die Enamin Funktion ist blau markiert. Enamine sind ungesättigte chemische Verbindungen,… …   Deutsch Wikipedia

  • enamine — enaminas statusas T sritis chemija formulė R₂NC(R)=CR₂ atitikmenys: angl. enamine rus. энамин …   Chemijos terminų aiškinamasis žodynas

  • enamine — noun Etymology: International Scientific Vocabulary en (alteration of ene) + amine Date: 1942 an amine containing the double bond linkage C=C–N …   New Collegiate Dictionary

  • enamine — en·a·mine (ĕnʹə mēn , ĭ nămʹēn) n. An amine that contains the double bond linkage ─C═C─N─R.   [en , chemically unsaturated (from ene) + amine.] * * * …   Universalium

  • enamine — noun Any of a class of unsaturated nitrogen compounds, having the general formula RC=C(R) NR, prepared by the condensation reaction of an aldehyde or ketone with an secondary amine; they are the tautomeric forms of imines …   Wiktionary

  • enamine — en·amine …   English syllables

  • enamine — noun an amine containing the double bond linkage C=C N • Hypernyms: ↑amine, ↑aminoalkane * * * ˈenəˌmēn, ˈēnəˌ , eˈnaˌm noun Etymology: en + amine (IV) : an amine containing the double bond linkage C=C−N …   Useful english dictionary

  • Stork enamine alkylation — Stork enamine alkylation, also known as the Stork Enamine reaction, involves the addition of an enamine to an alpha,beta unsaturated carbonyl acceptor in a process similar to the Michael reaction [cite book | last =McMurry | first =John |… …   Wikipedia

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