100-47-0Relevant articles and documents
Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides
Coombs, John R.,Fraunhoffer, Kenneth J.,Simmons, Eric M.,Stevens, Jason M.,Wisniewski, Steven R.,Yu, Miao
, p. 7040 - 7044 (2017)
Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twenty-two substituted benzonitriles have been synthesized using this method.
Oxidative conversion of amines into their corresponding nitriles using o-iodoxybenzoic acid (IBX)/iodine: Selective oxidation of aminoalcohols to hydroxynitriles
Chiampanichayakul, Supanimit,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima
, p. 2045 - 2048 (2008)
o-Iodoxybenzoic acid (IBX)/iodine in dimethyl sulfoxide at 65 °C oxidatively and efficiently converted various amines into the corresponding nitriles in good to excellent yields. Under the reaction conditions, amines were selectively oxidized to the nitrile in the presence of a primary hydroxy group within the same molecule. Thieme Stuttgart.
KINETICS OF REACTIONS OF O-(2,4-DINITROPHENYL) BENZALDOXIMES WITH METHYLAMINE, CYCLOHEXYLAMINE AND PIPERIDINE. REACTIVITY AT DIFFERENT ELECTROPHILIC SITES
Bhattacharjee, Gurudas,Singh, Ashok K.,Saikia, Ranjumoni
, p. 4537 - 4540 (1988)
Kinetics of reaction of E-O-(2,4-dinitrophenyl) benzaldoximes have been studied with MeNH2, cyclohexylamine (CHA) and piperdine (PiP) in 1:1 (v/v) ethanol-water at 35+/-0.1 deg C under pseudo first order conditions.The reactions are overall second order, first order with respect to each reactant.Hammett plots are linear with a ρ value of +0.75 for MeNH2, +0.61 for CHA and +1.25 for PiP.MeNH2 and CHA predominantly give the corresponding N-(2,4-dinitrophenyl)amine with attack at the aromatic carbon in sharp contrast to earlier observation with OH-.With piperidine both elimination and substitution products are obtained, the former product predominanting when strong electron-withdrawing substituents are present in the phenyl ring of the oxime.
Synthetic Reactions in Polyethylene Glycol. Diazotization and Sandmeyer Reactions of Anilines in Polyethylene Glycol-Methylene Dichloride
Suzuki, Nobutaka,Kaneko, Yoshihiro,Nomoto, Tateo,Izawa, Yasuji
, p. 1523 - 1524 (1984)
Diazotization and the Sandmeyer reactions of representative arylamines proceed smoothly in polyethylene glycol-CH2Cl2 and have been found to be effective for the preparation of aryl halides and cyanides.
Efficient synthesis of aromatic nitriles via cyanation of aryl bromides and K4[Fe(CN)6] catalyzed by a palladium(II) complex
Guo, Mengping,Ge, Junying,Zhu, Zhiyong,Wu, Xiaochun
, p. 213 - 215 (2013)
Cyanation of aryl bromides and K4[Fe(CN)6] were carried out in the presence of catalytic amounts of {[(PhCH2O) 2P(CH3)2CHNCH(CH3)2] 2PdCl2} (PdCl2L2) in DMF and a variety of Aromatic nitriles were obtained in good yields under aerobic conditions.
COMPARISON OF THE THERMAL AND MASS-SPECTROMETRIC FRAGMENTATION OF 2,4-THIOXO(OXO)DIHYDRO-5,6-BENZO-1,3-THIAZINES
Stach, I.,Herzschuh, R.,Leistner, S.,Wagner, H.
, p. 265 - 268 (1983)
The pyrolysis of a series of phenyl- and methyl-substituted 2,4-thioxo(oxo)dihydro-5,6-benzo-1,3-thiazines at the Curie point was studied.Processes involving retrodiene fragmentation with the formation of, respectively, phenyisothiocyanate or phenylisocyanate lie at the foundation of the thermal transformations of these compounds.Among other stable pyrolysis products, aniline, benzonitrile, and benzene were identified by gas chromatography and mass spectrometry.Pyrolysis directly in the mass spectrometer gives a larger number of fragmentation products, since it makes it possible to also record compounds with low stabilities.The results of the two methods of analysis correlate well with one another.
Reaction of Thioamides with Silver Carboxylates in Aprotic Media. A Nucleophilic Approach to the Synthesis of Imides, Amides, and Nitriles.
Avalos, Martin,Babiano, Reyes,Duran, Carlos J.,Jimenez, Jose L.,Palacios, Juan C.
, p. 477 - 480 (1994)
Synthesis of nitriles, imides, and amides by reaction of silver carboxylates with unsubstituted, N-substituted, and N,N-disubstituted thiomaides in aprotic media are described.
Rational catalysis design on the basis of mechanistic understanding: Highly efficient Pd-catalyzed cyanation of aryl bromides with NaCN in recyclable solvents
Ushkov, Alexander V.,Grushin, Vladimir V.
, p. 10999 - 11005 (2011)
Rational catalysis design on the basis of a detailed mechanistic understanding has been used to successfully develop the first efficient general Pd-catalyzed aromatic cyanation reaction under the highly sought after practicable conditions: (i) MCN (M = Na or K) as a cyanide source; (ii) low-boiling recyclable solvents; and (iii) minimal quantities of inexpensive, nontoxic promoters. The developed catalytic reaction converts aromatic bromides to the corresponding nitriles in 88-99% isolated yield with NaCN and 0.5-1.0 mol % of a t-Bu3P-monoligated Pd catalyst in MeCN-THF within 2 h at 70 °C. The process exhibits high functional group tolerance.
A base-induced ring-opening process of 2-substituted-1,3,4-oxadiazoles for the generation of nitriles at room temperature
Lu, Guo-Ping,Lin, Ya-Mei
, p. 371 - 374 (2014)
A novel base-catalysed 1,3,4-oxadiazole fragmentation for the synthesis of nitriles at room temperature has been developed. This reaction is performed under transition-metal-free conditions, and provides a new ring cleavage reaction of 1,3,4-oxadiazoles in organic synthesis.
Effect of Zn Substitutions in YBa2Cu3O6+x Phases on Reactivity during the Ammoxidation of Toluene
Otamiri, Jonathan C.,Andersson, Arne,Andersson, S. Lars T.,Crow, Jack E.,Gao, Ye
, p. 1265 - 1271 (1991)
Zn substitution in Y-Ba-Cu-O-phases influences the catalytic ammoxidation of toluene.The activity for formation of both benzonitrile and CO2 at low and high O2 pressures, respectively, decreases strongly with increasing Zn content up to 4percent.Above this substitution level, the activity, however, increases slightly.Characterisations of the surface by XPS and of the bulk by XRD analysis, indicate the presence of overlayers on the catalysts.In these overlayers, irrespective of the Zn content of catalysts, CuI states predominate at low O2 pressure and CuII at high pressure.These states are associated with selective and non-selective properties, respectively.The activity of the catalysts shows a general tendency to increase with surface copper concentrations as found from XPS studies.However, strong deviations from linearity indicate that the activity of the overlayer is greatly influenced by the bulk acting as a support.
