The relationship of imines to amines having double and single bonds can be correlated with imides and amides, as in succinimide vs acetamide. (wikipedia.org)
Imines are typically prepared by the condensation of primary amines and aldehydes. (wikipedia.org)
Rarer than primary amines is the use of ammonia to give a primary imine. (wikipedia.org)
Neat non-volatile amines react efficiently with various aromatic aldehydes in the absence of any catalyst or solvent, to give imines after a reaction time of eight minutes under microwave irradiation. (organic-chemistry.org)
Tris(2,2,2-trifluoroethyl)borate [B(OCH 2 CF 3 ) 3 ] is a mild and general reagent for condensation of amides or amines with carbonyl compounds providing N -Sulfinyl, N -toluenesulfonyl, N -(dimethylamino)sulfamoyl, N -diphenylphosphinoyl, N -(α-methylbenzyl), and N -(4-methoxyphenyl) aldimines at room temperature. (organic-chemistry.org)
In combination with polymer-supported cyanoborohydride (PSCBH), a one-pot oxidation-imine formation-reduction sequence enables alcohols to be converted directly into both secondary and tertiary amines. (organic-chemistry.org)
Imines and secondary amines were synthesized selectively by a Pd-catalyzed one-pot reaction of benzyl alcohols with primary amines. (organic-chemistry.org)
A modular aerobic oxidation of amines to imines has been achieved using an ortho -naphthoquinone ( o -NQ) catalyst. (organic-chemistry.org)
The oxidation of secondary amines to imines or ketimines is facilitated with the help of Ag 2 CO 3 as cocatalyst. (organic-chemistry.org)
Iron-catalyzed aerobic oxidative reactions of primary amines, secondary amines, benzylamines with anilines, and alcohols with amines in the presence of air as the economic and safe oxidant, provide several direct, practical, and greener approaches for the preparation of useful imines. (organic-chemistry.org)
A base-mediated protocol enables the synthesis of imines and amines from N -phenylureas and alcohols in good yields under air. (organic-chemistry.org)
This protocol is as an efficient alternative to conventional methods for the synthesis of imines and amines. (organic-chemistry.org)
The addition of 4 molecular sieves enables an efficient cobalt(II)-catalyzed N-alkylation of both aromatic and aliphatic amines with alcohols with high chemoselectivity (amines vs imines). (organic-chemistry.org)
Nitrogen4
In organic chemistry, an imine (/ɪˈmiːn/ or /ˈɪmɪn/) is a functional group or organic compound containing a carbon-nitrogen double bond (C=N). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. (wikipedia.org)
N-Sulfinyl imines are a special class of imines having a sulfinyl group attached to the nitrogen atom. (wikipedia.org)
A mild three-component reaction of aromatic aldehydes, alkyl bromides, and aqueous ammonia as the nitrogen source gives imines in very good yields. (organic-chemistry.org)
This side chain rotation results in a change in the pattern of hydrogen bonding connecting the mutant residue and the protonated Schiff base of the cofactor, which could account for the altered pK(a) of the Schiff base imine nitrogen that was reported previously. (weizmann.ac.il)
Ketimines1
For ketimines and aldimines, respectively, the five core atoms (C2C=NX and C(H)C=NX, X = H or C) are coplanar. (wikipedia.org)
Secondary3
When R = H, the compound is a primary imine, when R is hydrocarbyl, the compound is a secondary imine. (wikipedia.org)
a secondary imine with such groups is called a secondary aldimine. (wikipedia.org)
Primary aldimine, E-isomer Secondary aldimine, E-isomer Primary ketimine Secondary ketimine Aziridine and its derivatives are sometimes referred to as imines. (wikipedia.org)
Synthesis8
For example, benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis (lest the imine be hydrolyzed): C6H5CN + C6H5MgBr → (C6H5)2C=NMgBr (C6H5)2C=NMgBr + H2O → (C6H5)2C=NH + MgBr(OH) Several other methods exist for the synthesis of imines. (wikipedia.org)
R2C=NR' + H2O ⇌ R2C=O + R'NH2 Imines are widely used as intermediates in the synthesis of heterocycles. (wikipedia.org)
Imines react, thermally, with ketenes in [2+2] cycloadditions to form β-lactams in the Staudinger synthesis. (wikipedia.org)
Pyrrolidine as an organocatalyst enables a general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing an amino group. (organic-chemistry.org)
The method has been applied to the synthesis of N -sulfinyl, N -sulfonyl imines, N -phosphinoyl, N -alkyl, and N -aryl imines. (organic-chemistry.org)
The catalytic system can also be used for a one-pot synthesis of imines in excellent yield. (organic-chemistry.org)
This prompted us to investigate a biomimetic synthesis in which the halichonic acids could be prepared from a common imine intermediate via divergent intramolecular aza-Prins cyclizations [8] . (beilstein-journals.org)
The synthesis of β-lactams through imines requires a carbonyl compound and an amine. (springeropen.com)
Carbonyl2
The equilibrium in this reaction usually favors the carbonyl compound and amine, so that azeotropic distillation or use of a dehydrating agent, such as molecular sieves or magnesium sulfate, is required to favor of imine formation. (wikipedia.org)
The chief reaction of imines, often undesirable, is their hydrolysis back to the amine and the carbonyl precursor. (wikipedia.org)
Aldehydes2
Imines are related to ketones and aldehydes by replacement of the oxygen with an NR group. (wikipedia.org)
The reaction of aldehydes and aqueous ammonia with epoxides leads to imines bearing a vicinal hydroxyl group regioselectively. (organic-chemistry.org)
Aromatic1
Aromatic imines react with an enol ether to a quinoline in the Povarov reaction. (wikipedia.org)
Compounds2
Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. (wikipedia.org)
Usually imines refer to compounds with the general formula R2C=NR, as discussed below. (wikipedia.org)
Yield1
In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal -C(OH)(NHR)- intermediate, followed by an elimination of water to yield the imine (see alkylimino-de-oxo-bisubstitution for a detailed mechanism). (wikipedia.org)
Alcohols1
Manganese dioxide is employed as an in situ oxidant for the one-pot conversion of alcohols into imines. (organic-chemistry.org)
Reaction2
Imine react with dienes in the Imine Diels-Alder reaction to a tetrahydropyridine. (wikipedia.org)
The use of photosensitive C 70 for the catalytic oxidation of benzylamines to the corresponding imines enables faster reaction rates, lower catalyst loadings, and clean reactions with simple workup without chromatography, compared to C 60 or other commonly used photosensitizers such as tetraphenylporphyrin (TPP). (organic-chemistry.org)
Precursor1
To prepare α-aminonitriles (precursor to α-amino acids) generally an imine is reacted with a cyanide source. (springeropen.com)
Derivatives2
Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides. (tamu.edu)
In the older literature, imine refers to the aza-analogue of an epoxide. (wikipedia.org)
Formation2
In recent years, several reagents such as Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3], pyrrolidine or titanium ethoxide [Ti(OEt)4] have been shown to catalyse imine formation. (wikipedia.org)
Whereas the cooperative catalyst system of o -NQ and Cu(OAc) 2 provided homocoupled imines from benzylamines, the presence of TFA helped the formation of cross-coupled imines in excellent yields. (organic-chemistry.org)
Addition2
The utility of a Co III catalyst to promote the C2-selective addition of indoles to imines was demonstrated. (wiley.com)
Stoichiometric KO t Bu in THF enables an efficient transition metal-free approach for the generation of N -unsubstituted imines from azides. (organic-chemistry.org)
Selective2
With the appropriate choice of the ligand and other reaction conditions, ketimine- or aldimine-directed branched selective hydroarylations of styrenes and ketimine-directed hydroarylations of vinylsilane have been achieved. (ntu.edu.sg)
We have achieved efficient and selective difunctionalization of imines via CO2 activation by an N/B Lewis pair under copper catalysis. (nii.ac.jp)
Spectroscopy1
Using NMR spectroscopy, both E- and Z-isomers of aldimines have been detected. (wikipedia.org)
Carbon atom6
In organic chemistry, an imine (/ɪˈmiːn/ or /ˈɪmɪn/) is a functional group or organic compound containing a carbon-nitrogen double bond (C=N). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. (wikipedia.org)
C-13 chemical shifts of the azomethine carbon atom for N-(substituted phenyl)pyridine-4-aldimines, 4-Py-CH=N-C6H4-X, X having a wide range of substituent effects, have been determined in CDCl3 solution. (ac.rs)
Exceptionally good Hammett correlations of C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+) points out to a strong resonance interaction of substituents on the aniline ring with the azomethine carbon atom of the investigated imines. (ac.rs)
AU - Misić-Vuković, Milica AU - Marinković, Aleksandar AU - Vajs, Vlatka PY - 1999 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/257 AB - C-13 chemical shifts of the azomethine carbon atom for N-(substituted phenyl)pyridine-4-aldimines, 4-Py-CH=N-C6H4-X, X having a wide range of substituent effects, have been determined in CDCl3 solution. (ac.rs)
and Misić-Vuković, Milica and Marinković, Aleksandar and Vajs, Vlatka", year = "1999", abstract = "C-13 chemical shifts of the azomethine carbon atom for N-(substituted phenyl)pyridine-4-aldimines, 4-Py-CH=N-C6H4-X, X having a wide range of substituent effects, have been determined in CDCl3 solution. (ac.rs)
Jovanović BŽ, Misić-Vuković M, Marinković A, Vajs V. Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted) pyridine-4-aldimines. (ac.rs)
Mechanism1
In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal -C(OH)(NHR)- intermediate, followed by an elimination of water to yield the imine (see alkylimino-de-oxo-bisubstitution for a detailed mechanism). (wikipedia.org)
Intermediate1
My question regards tautomerization of this intermediate: has tautomerization between the two possible imine structures ever been observed, or is even possible? (stackexchange.com)