Imine

	Email		Print
	Bookmark		Link

Imine

:"Ketimine" redirects here. It should not be confused with "Ketamine
Ketamine

Ketamine is a drug used in human and veterinary medicine developed by Parke-Davis in 1962. Its hydrochloride salt is sold as Ketanest, Ketaset, and Ketalar....
" An imine is a functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
or chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
containing a carbon

Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
–nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
double bond . Due to their diverse reactivity, imines are common substrates in a wide variety of transformations. An imine can be synthesised by the nucleophilic addition

Nucleophilic addition

In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a p bond is removed by the creation of two new covalent bonds by the addition of a nucleophile ....
of an amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
to a ketone

Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
or aldehyde

Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
giving a hemiaminal

Hemiaminal

A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: -C-. R can be hydrogen or an alkyl group....
-C(OH)(NHR)- followed by an elimination

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism ....
of water to yield the imine.

Discussion

Ask a question about 'Imine'

Start a new discussion about 'Imine'

Answer questions from other users

Full Discussion Forum

Recent Posts

Preperation of oxime ethers

Has silver oxide been used as catalyst dor preparation of oxime ethers?

My compound has both imine group and ester group. I want to reduce ester to alcohol keeping imine un...

Encyclopedia

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
or chemical compound

Chemical compound

Carbon

Nitrogen

Nucleophilic addition

Amine

Ketone

Aldehyde

Hemiaminal

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism ....
of water to yield the imine. (see alkylimino-de-oxo-bisubstitution

Alkylimino-de-oxo-bisubstitution

Alkylimino-de-oxo-bisubstitution in organic chemistry is the organic reaction of carbonyl compounds with amines to imines . The reaction name is based on the IUPAC Nomenclature for Transformations....
for a detailed mechanism) However, the equilibrium in this reaction usually lies in favor of the free carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
compound and amine, so that azeotrope distillation or use of a dehydrating agent such as molecular sieve

Molecular sieve

A molecular sieve is a material containing tiny pores of a precise and uniform size that is used as an adsorption for gases and liquids.Molecules small enough to pass through the pores are adsorption while larger molecules are not....
s is required to push the reaction in favor of imine formation.

Addition reactions with primary amines give imines that are stable under an inert atmosphere. In the presence of oxygen or water, such imines will quite readily hydrolyze or oligomerize. However, with an aryl

Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
group or certain stabilizing alkyl

Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
substituent

Substituent

In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. The suffix -yl is used when naming organic compounds that contain a substituent....
s on nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
, the imine formed is stable to oxygen and water and is called a Schiff base

Schiff base

A Schiff base , named after Hugo Schiff, is a functional group that contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group?but not hydrogen ....
. In contrast, imine condensations using ammonia and a carbonyl compound do not lead to stable imines - the imine formed quickly oligomerizes such as in the reaction of formaldehyde

Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
and ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
which gives hexamine

Hexamine

Hexamine, also called hexamethylenetetramine or methenamine , is a heterocyclic organic compound that can be prepared by the chemical reaction of formaldehyde and ammonia....
instead of the corresponding imine. When a secondary amine is used, elimination of water from the hemiaminal leads to an iminium

Iminium

An iminium salt or cation in organic chemistry has the general structure [R1R2C=NR3R4]+ and is as such a protonation or Substitution reaction imine ....
ion. This iminium ion can further react to form either an aminal

Aminal

An aminal or aminoacetal is a functional group or type of chemical compound that has two amine groups attached to the same carbon atom: -C-....
, or enamine

Enamine

An enamine is an saturation compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O....
if there is an sp³-hybridized carbon in the alpha position. Addition of suitably activated carbonyl compounds to this imminium ion also leads to the corresponding Mannich base

Mannich base

A mannich base is an amine, which is formed in the reaction of electrophilic imine salt and enol of a carbonyl compound . Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of an aldehyde and any primary or secondary amine to produce resonance stabilized Schiff base ....
.

Imine synthesis

Several laboratory methods exist for the synthesis of imines.

Condensation of amines with carbonyls in alkylimino-de-oxo-bisubstitution
Alkylimino-de-oxo-bisubstitution

Alkylimino-de-oxo-bisubstitution in organic chemistry is the organic reaction of carbonyl compounds with amines to imines . The reaction name is based on the IUPAC Nomenclature for Transformations....
Condensation of carbon acids with nitroso
Nitroso

Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines....
compounds
The rearrangement of trityl N-haloamines in the Stieglitz rearrangement
Stieglitz rearrangement

The Stieglitz rearrangement is a rearrangement reaction of a trityl hydroxylamine Ar3CNHOH to a triaryl imine . The reaction is related to the Beckmann rearrangement as both reaction involve a carbon to nitrogen shift....
Dehydration
Dehydration

Dehydration is the removal of water from an object. In Physiology terms, it entails a relative deficiency of water molecules in relation to other dissolved solutes....
of hemiaminal
Hemiaminal

A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: -C-. R can be hydrogen or an alkyl group....
s
By reaction of alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
s with hydrazoic acid
Hydrazoic acid

Hydrazoic acid, hydrogennitrogen, is a colorless, volatile, and extremely explosive liquid at room temperature and pressure. It was first isolated in 1890 by Theodor Curtius....
in the Schmidt reaction
Schmidt reaction

The Schmidt reaction is an organic reaction involving alkyl migration over the carbon to nitrogen chemical bond in an azide with expulsion of nitrogen....
By reaction of a nitrile, hydrochloric acid and an arene in the Hoesch reaction

Imine reactions

An imine can be reduced to an amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
via hydrogenation
Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
for example in a synthesis of m-tolylbenzylamine:

An imine is also an intermediate in reductive amination

Reductive amination

Reductive amination is a chemical reaction which involves the conversion of a carbonyl group to an amine, via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde....
.

An imine can be hydrolysed
Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
with water to the corresponding amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
and carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
compound.
An imine reacts with an amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
to an aminal
Aminal

An aminal or aminoacetal is a functional group or type of chemical compound that has two amine groups attached to the same carbon atom: -C-....
, see for example the synthesis of cucurbituril
Cucurbituril

Cucurbiturils are Macrocycle consisting of glycoluril repeat units. These compounds are particularly interesting to chemists because they are molecular containers that are capable of binding other molecules within their cavities....
.
An imine reacts with diene
Diene

Dienes or diolefins are hydrocarbons which contain two covalent bond. Dienes are intermediate between alkenes and polyenes....
s in the Aza Diels-Alder reaction
Aza Diels-Alder reaction

The Aza Diels-Alder reaction converts imines and dienes to tetrahydropyridines. This organic reaction is a modification of the Diels-Alder reaction....
to a tetrahydropyridine.
An imine can be oxidized with meta-chloroperoxybenzoic acid
Meta-Chloroperoxybenzoic acid

meta-Chloroperoxybenzoic acid is a peroxycarboxylic acid used widely as an oxidant in organic synthesis. mCPBA is often preferred to other peroxy acids because of its relative ease of handling....
(mCPBA) to give an oxaziridine
An aromatic imine reacts with an enol ether
Enol ether

An enol ether is an alkene with an alkoxy substituent. The general structure is with R an alkyl or an aryl group. Enol ethers and enamines are so-called activated alkenes or electron rich alkenes because the oxygen atom donates electrons to the double bond by forming a resonance structure with the corresponding oxonium ion....
to a quinoline
Quinoline

Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour....
in the Povarov reaction
Povarov reaction

The Povarov reaction is a chemical reaction described as a formal cycloaddition between an aromatic imine and an alkene. The imine in this organic reaction is a condensation reaction product from an aniline type compound and a benzaldehyde type compound ....
.
A tosyl
Tosyl

A tosyl group is CH3C6H4SO2. This group is usually derived from the compound 4-Toluenesulfonyl chloride, CH3C6H4SO2Cl, which forms esters and amides of toluenesulfonic acid....
imine reacts with an a,ß-unsaturated carbonyl compound to an allyl
Allyl

An allyl group is an alkene hydrocarbon group with the formula H2C=CH-CH2-. It is made up of a vinyl group, CH2=CH-, attached to a methylene -CH2....
ic amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
in the Aza-Baylis-Hillman reaction
Aza-Baylis-Hillman reaction

The Aza-Baylis-Hillman reaction or aza-BH reaction in organic chemistry is a variation of the Baylis-Hillman reaction and describes the reaction of an electron deficient alkene usually an a,?-unsaturated carbonyl compound with an imine in the presence of a nucleophile....
.
Imines are intermediates in the alkylation of amines with formic acid in the Eschweiler-Clarke reaction
Eschweiler-Clarke reaction

The Eschweiler-Clarke reaction is a chemical reaction whereby a primary amine is methylated using excess formic acid and formaldehyde. Reductive amination reactions such as this one will not produce quaternary ammonium salts, but instead will stop at the tertiary amine stage....
.
A rearrangement in carbohydrate chemistry involving an imine is the Amadori rearrangement
Amadori rearrangement

The Amadori rearrangement is an organic reaction describing the acid catalysis isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose....
.
A methylene transfer reaction of an imine by an unstabilised sulphonium ylide
Ylide

An ylid or ylide is a electric charge molecule with a positive and a negative charge on adjacent atoms. They appear in organic chemistry as reagents or reactive intermediates....
can give an aziridine
Aziridine

Aziridines are a group of organic compounds sharing the aziridine functional group which is a three membered heterocycle with one amine group and two methylene groups....
system.

Amidates

imidates (also known as imino ethers) (R-N=C(OR)R) are imines with an oxygen atom connected to carbon. These compounds find use in organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
as building blocks and intermediates for example in the Mumm rearrangement

Mumm rearrangement

The Mumm rearrangement is an organic reaction and a rearrangement reaction . It describes a 1,3 acyl transfer of an acyl imidate or isoimide group to an imide....
and the Overman rearrangement

Overman rearrangement

The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides through an imidate intermediate....
. An example of an imidate is benzyl 2,2,2-trichloroacetimidate used to protect an alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
as a benzyl ether with release of trichloroacetamide.

Amidates are the corresponding amide

Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
enolates: R-N=C(O^-)R and find use as ligand

Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
s.

Imine

Imine synthesis

Imine reactions

Amidates

See also