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78-97-7Relevant academic research and scientific papers
Photoiodocarboxylation of Activated C=C Double Bonds with CO2 and Lithium Iodide
Mello, Rossella,Arango-Daza, Juan Camilo,Varea, Teresa,González-Nú?ez, María Elena
, p. 13381 - 13394 (2018/11/20)
The photolysis at 254 nm of lithium iodide and olefins 1 carrying an electron-withdrawing Z-substituent in CO2-saturated (1 bar) anhydrous acetonitrile at room temperature produces the atom efficient and transition metal-free photoiodocarboxylation of the C=C double bond. The reaction proceeds well for terminal olefins 1 to form the new C-I and C-C σ-bonds at the α and β-positions of the Z-substituent, respectively, and is strongly inhibited by polar protic solvents or additives. The experimental results suggest that the reaction channels through the radical anion [CO2?-] in acetonitrile, yet involves different intermediates in aqueous medium. The stabilizing ion-quadrupole and electron donor-acceptor interactions of CO2 with the iodide anion play a crucial role in the reaction course as they allow CO2 to penetrate the solvation shell of the anion in acetonitrile, but not in water. The reaction paths and the reactive intermediates involved under different conditions are discussed.
Photochemical reductive homologation of hydrogen cyanide using sulfite and ferrocyanide
Xu, Jianfeng,Ritson, Dougal J.,Ranjan, Sukrit,Todd, Zoe R.,Sasselov, Dimitar D.,Sutherland, John D.
supporting information, p. 5566 - 5569 (2018/06/04)
Photoredox cycling during UV irradiation of ferrocyanide ([FeII(CN)6]4-) in the presence of stoichiometric sulfite (SO32-) is shown to be an extremely effective way to drive the reductive homologation
2 - methyl malonic acid diester synthetic method of the compound
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Paragraph 0033-0036, (2017/08/10)
The invention discloses a synthetic method of 2-diester methylmalonate compounds, and relates to the technical field of carboxylic ester preparation. The synthetic method comprises steps as follows: C, sulfonic acid 2-ethyl N-cyanoethanimideate IV and cyanide react under the action of a solvent and a catalyst, and 2-methyl malononitrile V is obtained; D, 2-methyl malononitrile V and ROH react under the action of the solvent and concentrated sulfuric acid, and products of 2-diester methylmalonate compounds I are obtained, wherein MCN is cyanide, M is Na or K, ROH is alkyl alcohol, alkenyl alcohol or a fluoride group containing alcohol, is benzyl alcohol or benzyl alkyl, halogen or nitro substituted benzyl alcohol, or is phenol or C1-C5 containing alkyl, halogen or nitro substituted phenol. The method is unique, the reaction conditions are mild, the reaction process is basically free of by-products, the yield is high, adopted raw materials have extensive sources, and acetaldehyde can be used as the raw material; the synthetic method is applicable to industrial production.
Preparation method of 2-hydroxy acid ester
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Paragraph 0034-0035, (2017/04/11)
The invention relates to a preparation method of 2-hydroxy acid ester and belongs to the technical field of organic synthesis. According to the preparation method of 2-hydroxy acid ester, 2-hydroxy alkyl cyanogens is taken as a raw material to be added to a reaction solution formed by hydrogen chloride, alcohol and water, and after reaction, 2-hydroxy acid ester is obtained. According to the preparation method of 2-hydroxy acid ester, use of a large amount of nonpolar solvent is not needed, and a target product can be obtained by a one-pot method, thus lowering production cost, improving production efficiency and the purify of the target product, and having energy-saving and environment-friendly effects.
Method of manufacturing cyanohydrins
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Paragraph 0072; 0073, (2016/12/26)
Disclosed is a process for producing a cyanohydrin, the process comprising reacting a carbonyl compound with hydrocyanic acid in a buffer solution with a pH less than 7 to obtain the cyanohydrin.
Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles
Kadunce, Nathaniel T.,Reisman, Sarah E.
supporting information, p. 10480 - 10483 (2015/09/28)
A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.
Hydration of alkenes and cycloalkenes in the presence of chromium and copper complexes
Khusnutdinov,Oshnyakova,Shchadneva
, p. 1428 - 1432 (2014/01/06)
Chromium and copper complexes catalyzed hydration of acyclic and cyclic olefins in the presence of carbon tetrachloride at 110-160 C (4-12 h) with formation of the corresponding alcohols.
Synthesis of aldehydic ribonucleotide and amino acid precursors by photoredox chemistry
Ritson, Dougal J.,Sutherland, John D.
supporting information, p. 5845 - 5847 (2013/07/11)
Light work: UV irradiation of a system formed by adding copper(I) cyanide to an aqueous solution of glycolonitrile, sodium phosphate, and hydrogen sulfide efficiently generates aldehyde precursors to the building blocks of RNA and proteins. Copyright
Tautomer selective photochemistry in 1-(tetrazol-5-yl)ethanol
Ismael,Cristiano,Fausto,Gomez-Zavaglia
experimental part, p. 13076 - 13085 (2011/03/01)
A combined matrix isolation FTIR and theoretical DFT/B3LYP/6-311++G(d,p) study of the molecular structure and photochemistry of 1-(tetrazol-5-yl)ethanol [1-TE] was performed. The potential energy surface landscapes of the 1H and 2H tautomers of the compound were investigated and the theoretical results were used to help characterize the conformational mixture existing in equilibrium in the gas phase prior to deposition of the matrices, as well as the conformers trapped in the latter. In the gas phase, at room temperature, the compound exists as a mixture of 12 conformers (five of the 1H tautomer and seven of the 2H tautomer). Upon deposition of the compound in an argon matrix at 10 K, only three main forms survive, because the low barriers for conformational isomerization allow extensive conformational cooling during deposition. Deposition of the matrix at 30 K led to further simplification of the conformational mixture with only one conformer of each tautomer of 1-TE surviving. These conformers correspond to the most stable forms of each tautomer, which bear different types of intramolecular H-bonds: 1H-I has an NH···O hydrogen bond, whereas 2H-I has an OH···N hydrogen bond. Upon irradiating with UV light (λ > 200 nm), a matrix containing both 1H-I and 2H-I forms, an unprecedented tautomer selective photochemistry was observed, with the 2H tautomeric form undergoing unimolecular decomposition to azide + hydroxypropanenitrile and the 1H-tautomer being photostable.
Chiral solvating agents for cyanohydrins and carboxylic acids
Moon, Lomary S.,Pal, Mohan,Kasetti, Yoganjaneyulu,Bharatam, Prasad V.,Jolly, Ravinder S.
body text, p. 5487 - 5498 (2010/11/05)
We have shown that a structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Moreover, 1H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chemical shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH+ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M-1 (ΔG 0, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH + and 139 M-1 (ΔG0, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH+ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)- mandelate/DMAPH+ and (S)-mandelonitrile/(S)-mandelate/DMAPH + complexes was performed using DFT methodology (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, analysis of optimized molecular model obtained from theoretical studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as methyl, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were experimentally verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.