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Reactions of enamines and enolates (1)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (2)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (3)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (4)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (5)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (6)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (7)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (8)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (9)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (10)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (11)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (12)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (13)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (14)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (15)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (16)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (17)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (18)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (19)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Imine and Enamine Formation
The mechanisms of imine and enamine formation are presented.
Reactions of enamines and enolates (20)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (21)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Reactions of enamines and enolates (22)
Organic chemistry: Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation;...
Enamine
An
enamine is an
unsaturated compound derived by the reaction of an
aldehyde or
ketone with a secondary
amine followed by loss of H
2O.
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.
If one of the nitrogen substituents is a hydrogen atom, 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 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.
References
See also
Thorpe reaction
Category:Functional groups
Category:Enamines
This text is licensed under the Creative Commons CC-BY-SA License. This text was originally published on Wikipedia and was developed by the Wikipedia community.
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