Our website is made possible by displaying online advertisements to our visitors.
Please consider supporting us by disabling your ad blocker.
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. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols.[6]
If one or both of the nitrogen substituents is a hydrogen atom 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 tautomerism 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.
Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following resonance structures.
- ^ Clayden, Jonathan (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 978-0-19-850346-0.
- ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
- ^ Enamines: Synthesis: Structure, and Reactions, Second Edition, Gilbert Cook (Editor). 1988, Marcel Dekker, NY. ISBN 0-8247-7764-6
- ^ R. B. Woodward, I. J. Pachter, and M. L. Scheinbaum (1974). "2,2- (Trimethylenedithio)cyclohexanone". Organic Syntheses. 54: 39
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 1014. - ^ R. D. Burpitt and J. G. Thweatt (1968). "Cyclodecanone". Organic Syntheses. 48: 56; Collected Volumes, vol. 5, p. 277.
- ^ Imines and Enamines | PharmaXChange.info
Previous Page Next Page
