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De Kimpe Aziridine Synthesis
The De Kimpe azirdine synthesis is a name reaction of organic chemistry, for the generation of aziridines by the reaction of α-chloroimines with nucleophiles such as hydride, cyanide, or Grignard reagents A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . .... The De Kimpe aziridine synthesis is suitable for both aldimines and ketamines, particularly those with two alkyl substituents on the α-carbon ( Thorpe-Ingold effect). Mechanism The nucleophile attacks the imino carbon atom, forming a tetrahedral intermediate. The intermediate then undergoes an intramolecular nucleophilic substitution, with the negatively charged nitrogen atom attacking the α-carbon and having the chloride anion as the leaving group. References Name reactions {{chemistry-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Name Reaction
A name reaction is a chemical reaction named after its discoverers or developers. Among the tens of thousands of organic reactions that are known, hundreds of such reactions are well-known enough to be named after people. Well-known examples include the Grignard reaction, the Sabatier reaction, the Wittig reaction, the Claisen condensation, the Friedel-Crafts acylation, and the Diels-Alder reaction. Books have been published devoted exclusively to name reactions;Alfred Hassner, C. Stumer. ''Organic syntheses based on name reactions''. Elsevier, 2002. Li, Jie Jack. ''Name Reactions: A Collection of Detailed Reaction Mechanisms''. Springer, 2003. the Merck Index, a chemical encyclopedia, also includes an appendix on name reactions. As organic chemistry developed during the 20th century, chemists started associating synthetically useful reactions with the names of the discoverers or developers; in many cases, the name is merely a mnemonic. Some cases of reactions that were not really ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aziridines
220 px, chemotherapeutic agent by virtue of its antitumour activity. Aziridines are organic compounds containing the aziridine functional group, a three-membered heterocycle with one amine (-NR-) and two methylene bridges (--). The parent compound is aziridine (or ethylene imine), with molecular formula . Several drugs feature aziridine rings, including mitomycin C, porfiromycin, and azinomycin B (carzinophilin). Structure The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of sepa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. Structure For ketimines and aldimines, respectively, the five core atoms (C2C=NX and C(H)C=NX, X = H or C) are coplanar. Planarity results from the sp2-hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29-1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C-N distances in amines and nitriles are 1.47 and 1.16 Å, respectively. Rotation about the C=N bond is slow. Using NMR spectroscopy, both E- and Z-isomers of aldimines have been detected. Owing to steric effects, the E isomer is favored. Nomenclature and classification The term "imine" was coine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydride
In chemistry, a hydride is formally the anion of hydrogen( H−). The term is applied loosely. At one extreme, all compounds containing covalently bound H atoms are called hydrides: water (H2O) is a hydride of oxygen, ammonia is a hydride of nitrogen, etc. For inorganic chemists, hydrides refer to compounds and ions in which hydrogen is covalently attached to a less electronegative element. In such cases, the H centre has nucleophilic character, which contrasts with the protic character of acids. The hydride anion is very rarely observed. Almost all of the elements form binary compounds with hydrogen, the exceptions being He, Ne, Ar, Kr, Pm, Os, Ir, Rn, Fr, and Ra. Exotic molecules such as positronium hydride have also been made. Bonds Bonds between hydrogen and the other elements range from highly to somewhat covalent. Some hydrides, e.g. boron hydrides, do not conform to classical electron-counting rules and the bonding is described in terms of multi-centered ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyanide
Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. In inorganic cyanides, the cyanide group is present as the anion . Soluble salts such as sodium cyanide (NaCN) and potassium cyanide (KCN) are highly toxic. Hydrocyanic acid, also known as hydrogen cyanide, or HCN, is a highly volatile liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts. Organic cyanides are usually called nitriles. In nitriles, the group is linked by a covalent bond to carbon. For example, in acetonitrile (), the cyanide group is bonded to methyl (). Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus rather toxic. Bonding The cyanide ion is isoelectronic with carbon monoxide a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reagents
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents. Pure Grignard reagents are extremely reactive solids. They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a complex with the magnesium atom connect ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
