Imine

An imine is a functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

or chemical compound containing a carbon Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ...

-nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ...

double bond Covalent bond

Covalent bonding is an intramolecular form of chemical bond [i]ing characterized by the sharing of one o ...

. An imine can be synthesised by nucleophilic addition from a ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i] ...

or aldehyde Aldehyde

An aldehyde is an organic compound containing ...

and ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ...

or an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

to a hemiaminal Hemiaminal

A hemiaminal is a functional group [i] or type of chemical compound [i] that has a hydroxyl group [i] an ...

-C- followed by elimination Elimination reaction

An elimination reaction is a type of organic reaction [i] in which two substituent [i]s are removed from ...

of water to the imine.

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Encyclopedia

An imine is a functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

or chemical compound containing a carbon Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ...

-nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ...

double bond Covalent bond

Covalent bonding is an intramolecular form of chemical bond [i]ing characterized by the sharing of one o ...

. An imine can be synthesised by nucleophilic addition from a ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i]...

or aldehyde Aldehyde

An aldehyde is an organic compound containing
...

and ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ...

or an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

to a hemiaminal Hemiaminal

A hemiaminal is a functional group [i] or type of chemical compound [i] that has a hydroxyl group [i] an ...

-C- followed by elimination Elimination reaction

An elimination reaction is a type of organic reaction [i] in which two substituent [i]s are removed from ...

of water to the imine.

Imine synthesis

The addition of ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ...

to an aldehyde Aldehyde

An aldehyde is an organic compound containing

...

or ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i]...

does not lead to a stable imine. The reaction of formaldehyde Formaldehyde

The chemical compound [i] formaldehyde , is a gas [i] with a pungent smell. ...

and ammonia yields hexamine Hexamine

Hexamine, also called methenamine, is a heterocyclic organic compound [i] that can be prepared by ...

. Imine formation generally takes place fastest between pH 4 and 5 and is slow at very low or very high pH.

Addition reactions with primary amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

s give stable imines
but with an aryl group or certain stabilizing alkyl Alkyl

An alkyl is a univalent [i] radical [i] containing only carbon [i] and hydrogen [i] atoms arrang ...

substituents on nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ...

, the imine is truly stable, see alkylimino-de-oxo-bisubstitution Alkylimino-de-oxo-bisubstitution

Alkylimino-de-oxo-bisubstitution in organic chemistry [i] is the organic reaction [i] of carbonyl [i] co ...

.
A secondary amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

lacks hydrogen and elimination of water is not possible. The hemiaminal intermediate is not stable and

with no alpha hydrogen present it proceeds to form an aminal Hemiaminal

A hemiaminal is a functional group [i] or type of chemical compound [i] that has a hydroxyl group [i] an ...
with alpha hydrogen present it proceeds to form an enamine Enamine

An enamine is an unsaturated [i] compound derived by the reaction of an aldehyde [i] or ketone [i] ...

note that addition of carbonyl compounds to the salt of an amine yields the corresponding Mannich base Mannich base

A mannich base is the reaction product of an amine [i] and a carbonyl [i] compound that engage in a nucleophilic addition [i] ...
imine formation is part of the Friedl�nder synthesis Friedl�nder synthesis

...

of quinolines.

Imine reactions

an imine can be reduced Redox

Redox reactions include all chemical processes [i] in which atoms have their oxidation number [i] ...

to an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...
an imine can be hydrolysed Hydrolysis

Hydrolysis is a chemical reaction [i] or process in which a molecule [i] is split into two parts by reac ...

with water to the corresponding amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

and carbonyl Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]...

compound
an imine reacts with an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

to an aminal Hemiaminal

A hemiaminal is a functional group [i] or type of chemical compound [i] that has a hydroxyl group [i] an ...

, see for example the synthesis of cucurbituril Cucurbituril

Cucurbiturils are macrocyclic molecules consisting of glycoluril [i] repeat units. ...

.
an imine reacts with dienes in the Aza Diels-Alder reaction Aza Diels-Alder reaction

The Aza Diels-Alder reaction converts imine [i]s and diene [i]s to tetrahydropyridine [i]s. ...

to a tetrahydropyridine.
an aromatic imine reacts with an enol ether to a quinoline Quinoline

Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic [i] ...

in the Povarov reaction Povarov reaction

The Povarov reaction is a formal cycloaddition [i] between an aromatic [i] imine [i] and an alkene [i]....
A tosyl Tosyl

A tosyl group combines the toluene [i] and sulfonyl [i] functional groups [i]. ...

imine reacts with an a,�-unsaturated carbonyl compound to an allylic Allyl

[i]

...

amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ...

in the Aza-Baylis-Hillman reaction Aza-Baylis-Hillman reaction

The Aza-Baylis-Hillman reaction or aza-BH reaction in organic chemistry [i] is a variation of the...

imines are intermediates in the alkylation of amines with formic acid in the Eschweiler-Clarke reaction Eschweiler-Clarke reaction

The Eschweiler-Clarke reaction [i] is a chemical reaction [i] whereby a primary amine [i] is methylated [i] us ...

References