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102-82-9Relevant articles and documents
Effect of the catalyst preparation method on the performance of Ni-supported catalysts for the synthesis of saturated amines from nitrile hydrogenation
Segobia,Trasarti,Apesteguía
, p. 1693 - 1703 (2019)
The liquid-phase hydrogenation of butyronitrile to saturated amines was studied on silica-supported Ni catalysts prepared by either incipient-wetness impregnation (Ni/SiO2-I) or ammonia (Ni/SiO2-A) methods. A Ni/SiO2-Al2O3-I sample was also used. Ni/SiO2-I was a non-acidic catalyst containing large Ni0 particles of low interaction with the support, while Ni/SiO2-A was an acidic catalyst due to the presence of Ni2+ species in Ni phyllosilicates of low reducibility. Ni/SiO2-I formed essentially butylamine (80%), and dibutylamine as the only byproduct. In contrast, Ni/SiO2-A yielded a mixture of dibutylamine (49%) and tributylamine (45%), being the formation of butylamine almost completely suppressed. The selective formation of secondary and tertiary amines on Ni/SiO2-A was explained by considering that butylamine is not release to the liquid phase during the reaction because it is strongly adsorbed on surface acid sites contiguous to Ni0 atoms, thereby favoring the butylimine/butylamine condensation to higher amines between adsorbed species.
Deoxygenation of amine N-oxides using gold nanoparticles supported on carbon nanotubes
Donck, Simon,Gravel, Edmond,Shah, Nimesh,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
, p. 50865 - 50868 (2015)
Deoxygenation of a variety of aromatic and aliphatic amine N-oxides has been carried out in excellent yield using dimethylphenylsilane as the reducing agent under the catalytic influence of a carbon nanotube-gold nanohybrid at room temperature. Low catalyst loading, good TON and TOF values, and recyclability of the catalyst are some of the salient features of our methodology.
Selective deoxygenation of amine N-oxides using borohydride exchange resin-copper sulfate in methanol
Sim, Tae Bo,Ahn, Jin Hee,Yoon, Nung Min
, p. 324 - 326 (1996)
Borohydride exchange resin-copper sulfate in methanol readily deoxygenates quantitatively both tertiary amine N-oxides and heteroaromatic N-oxides at room temperature or under reflux. It tolerates many functional groups such as carbon-carbon double bond, chloride, epoxide, ester, amide, nitrile, sulfoxide, sulfone, and aliphatic disulfide moieties.
RUTHENIUM CATALYZED N-ALKYLATION OF AMIDES WITH ALCOHOLS.
Watanabe,Ohta,Tsuji
, p. 2647 - 2651 (1983)
Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl//2(PPh//3)//3 at 180 degree C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with l-octanol to give N-octylbenzamide in 76% yield with excellent product selectivity. Little esterification of amides with alcohols occurred and selectivity to the N-alkylation was high. Most of the amides gave N-monoalkyl amides but no N,N-dialkyl amides. But formamide reacted with l-butanol to give N,N-dibutylformamide, as well as N-butylformamide, in low yield. RuCl//2(PPh//3)//3 was the most effective catalyst for this reaction and RuHCl(PPh//3)//3 also had some catalytic activity.
Iodide-mediated or iodide-catalyzed demethylation and friedel-crafts C-H borylative cyclization leading to thiophene-fused 1,2-oxaborine derivatives
Shigemori, Keisuke,Watanabe, Momoka,Kong, Julie,Mitsudo, Koichi,Wakamiya, Atsushi,Mandai, Hiroki,Suga, Seiji
, p. 2171 - 2175 (2019)
The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2′-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.
Hofmann Decomposition of Queternary Ammonium Salts under Phase-transfer Catalytic Conditions
Zerda, Jaime de la,Neumann, Ronny,Sasson, Yoel
, p. 823 - 826 (1986)
The known Hofmann degradation of quaternary ammonium salts under basic phase-transfer catalytic conditions has been studied.The base-catalysed isomerization of p-allylanisole to p-methoxy-β-methylstyrene was used as a kinetic probe to find experimentally the rate constant and activation energy of the Hofmann decomposition without isolating the quaternary ammonium basic salt R4N+B- (B- = base anion).Reactions performed at various temperatures showed that the higher the temperature the greater was the initial rate but the lower the final conversion in the isomerization reaction.The quaternary ammonium hydroxide was found to catalyse the isomerization and the Hofmann degradation more effectively than the corresponding alkoxide.This indicates that the former is a stronger base in the non-polar aprotic solvents common in phase-transfer catalysis.
Decomposition mechanism of dinitramide onium salts
Pavlov,Nazin
, p. 1848 - 1850 (1997)
Thermal decomposition of dinitramide onium salts proceeds via the dissociative mechanism when pKa of the base is lower than 5.0 and via the monomolecular decay of the anion at pKa > 7.0. On going from the melt to the solid state, the reaction mechanism does not change, and the rate decreases by 1-2 orders of magnitude. No anomalous effects inherent in dinitramide metal salts in the solid phase are observed during decomposition of onium salts.
Synthesis of n-butylamine from butyronitrile on Ni/SiO2: Effect of solvent
Segobia, Darío J.,Trasarti, Andrés F.,Apesteguía, Carlos R.
, p. 2272 - 2279 (2014)
The effect of solvent on Ni(10.5percent)/SiO2 activity and selectivity for the liquid-phase hydrogenation of butyronitrile to butylamines was studied at 373 K and 13 bar using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84percent) and dibutylamine (16percent). When non-polar solvents, such as cyclohexane, toluene or benzene, were used, the solvent-catalyst interaction strength determined the selectivity to n-butylamine: the stronger the solvent-catalyst interaction the higher the n-buylamine production. The yield to n-butylamine in non-polar solvents varied between 39percent (cyclohexane) and 63percent (benzene).
Electrolytic Reduction of 1,4-Dihalonorbornanes at Mercury Electrodes in Dimethylformamide. Evidence for Propellane as an Intermediate
Carroll, William F.,Peters, Dennis G.
, p. 4127 - 4134 (1980)
Low-temperature (-34 deg C) electrolytic reduction of 1,4-dibromonorbornane at mercury cathodes in dimethylformamide containing tetraalkylammonium perchlorates yields norbornane, bis(1-norbornyl)mercury, and 1,1'-binorbornyl; reduction of 1,4-diiodonorbornane results in the same three products along with 1-iodonorbornane and other minor species.At potentials for which the mass balance is 100percent, norbornane and bis(1-norbornyl)mercury account for 98percent of the electrolysis products and the coulometric n value is precisely three.When tetramethylammonium perchlorate is utilized as the supporting electrolyte at -34 deg C, there is a range of potentials over which a pronounced polarographic current minimun appears; this low-temperature minimum is attributed to adsorbtion upon the electrode of complex species consisting of tetramethylammonium cations and halide ions.Three key observations suggest that propellane is an intermediate in the electrochemical reduction of the 1,4-dihalonorbornanes: (1) norbornane is derived from 1,4-dihalonorbornane via a three-electron process which does not involve 1-halonorbornane as intermediate; (2) bis(1-norbornyl)mercury is produced by electrolytic reduction of 1,4-dihalonorbornane but not by reduction of 1-halonorbornane; and (3) a species apparently obtained by two-electron reduction of 1,4-dihalonorbornanes is capable of undergoing oligomerization.A polarographic wave seemingly attributable to reduction of propellane is observed.
ELECTROCHEMICAL REDUCTION OF TRIPHENYL PHOSPHATE
Yanilkin, V. V.,Budnikova, Yu. G.,Kargin, Yu. M.,Gritsenko, E. I.,Strelets, V. V.
, p. 1149 - 1152 (1990)
The electrolytic reduction of triphenyl phosphate proceeds with the participation of tetrabutylammonium cations with the formation of butyl diphenyl phosphate in DMF.It was concluded that the step involving electron transfer to the triphenyl phosphate molecule has retarded character.