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Amine-carbonyl Condensation
In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. The reaction name is based on the IUPAC Nomenclature for Transformations. The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines, water is lost in an elimination reaction to an imine. With aryl amines, especially stable Schiff bases are formed. Reaction mechanism The reaction steps are reversible reactions and the reaction is driven to completion by removal of water e.g. by azeotropic distillation, molecular sieves or titanium tetrachloride. Primary amines react through an unstable hemiaminal intermediate which then splits off water. : Secondary amines do not lose water easily because they do not have a proton available and instead they often react further to an aminal: : or w ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Titanium Tetrachloride
Titanium tetrachloride is the inorganic compound with the formula . It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide () and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4", as a phonetic representation of the symbols of its molecular formula (). Properties and structure is a dense, colourless liquid, although crude samples may be yellow or even red-brown. It is one of the rare transition metal halides that is a liquid at room temperature, being another example. This property reflects the fact that molecules of weakly self-associate. Most metal chlorides are polymers, wherein the chloride atoms bridge between the metals. Its melting point is similar to that of . has a "closed" electronic shell, with the same number of electrons as the nobl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Structure and bonding Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The bond length is about 120–122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are solubl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Protective Group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, specific parts of the molecules cannot survive the required reagents or chemical environments. These parts (functional groups) must be protected. For example, lithium aluminium hydride is a highly reactive reagent that usefully reduces esters to alcohols. It always reacts with carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must be prevented. One way to do so converts the carbonyl into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the hydride step is complete, aqueous acid removes the acetal, restoring the carbonyl. This step i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aminoaldehydes And Aminoketones
Aminoaldehydes and aminoketones are organic compounds that contain an amine functional group as well as either a aldehyde or ketone functional group. These compounds are important in biology and in chemical synthesis. Because of their bifunctional nature, they have attracted much attention from chemists. Tertiary amine derivatives Because primary and secondary amines react with aldehydes and ketones, the most common variety of these aminocarbonyl compounds feature tertiary amines. Such compounds are produced by amination of α- haloketones and α- haloaldehydes. Examples include cathinones, methadone, molindone, pimeclone, ferruginine, and tropinone. Secondary amine derivatives Aminoketones containing secondary amines are typically stable when the ketone is located on a ring, e.g. 4-piperidinone, triacetonamine, acridone. Primary amine derivatives Most members of this class are unstable towards self-condensation, however some important examples do exist as intermediates in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, st ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Povarov Reaction
The Povarov reaction is an organic 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. The alkene must be electron rich which means that functional groups attached to the alkene must be able to donate electrons. Such alkenes are enol ethers and enamines. The reaction product in the original Povarov reaction is a quinoline. Because the reactions can be carried out with the three components premixed in one reactor it is an example of a multi-component reaction. : Reaction mechanism The reaction mechanism for the Povarov reaction to the quinoline is outlined in Scheme 1. In step one aniline and benzaldehyde react to the Schiff base in a condensation reaction. The Povarov reaction requires a Lewis acid such as boron trifluoride to activate the imine for an electrophilic addition of the activated alkene. This reaction step ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Heterocycle
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Iminium
In organic chemistry, an iminium cation is a polyatomic ion with the general structure . They are common in synthetic chemistry and biology. Structure Iminium cations adopt alkene-like geometries: the central C=N unit is nearly coplanar with all four substituents. Unsymmetrical iminium cations can exist as cis and trans isomers. The C=N bonds, which are near 129 picometers in length, are shorter than C-N single bonds. Cis/trans isomers are observed. The C=N distance is slightly shorter in iminium cations than in the parent imine, and computational studies indicate that the C=N bonding is also stronger in iminium vs imine, although the C=N distance contracts only slightly. These results indicate that the barrier for rotation is higher than in the parent imines. Formation Iminium cations are obtained by protonation and alkylation of imines: : : They also are generated by the condensation of secondary amines with ketones or aldehydes: : This rapid, reversible reaction is one ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enamine
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. 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 (chemistry), alcohol (-''ol''). Enamines are considered to be nitrogen analogs of enols. 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 t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
