14181-75-0Relevant academic research and scientific papers
One-pot reductive amination of araldehydes by aniline using borohydride with CeCl3·7H2O as catalyst
Zhu, Xun,Zhou, Xiuqin,Zhang, Wei
, p. 390 - 393 (2015/08/18)
A one-pot, two-step reductive amination of araldehydes or acetophenones with anilines using NaBH4as a cheap hydride source and catalysed by CeCl3·7H2O has been achieved in EtOH at room temperature in good yields.
The Diels-Alder cyclization of ketenimines
Erb, Jeremy,Strull, Jessica,Miller, David,He, Jean,Lectka, Thomas
supporting information; experimental part, p. 2191 - 2193 (2012/07/27)
A Diels-Alder reaction between cyclopentadiene and a variety of ketenimines is reported. A copper(I)-bis(phosphine complex catalyzes the cycloaddition across the C - N bond of the ketenimine in a [4 + 2] reaction to give an enamine intermediate that is hy
Kinetics and mechanism of gas-phase pyrolysis of ylides. Part 3. 1 Thermal reactivity of α-carbonyl- and thiocarbonyl-stabilized methylenetriphenylphosphoranes
Al-Bashir, Rasha F.,Al-Awadi, Nouria A.,El-Dusouqui, Osman M. E.
scheme or table, p. 311 - 319 (2012/04/17)
Fourteen ketone/thione-stabilized triphenylphosphonium methylides were subjected to conventional gas-phase and flash vacuum pyrolysis (FVP). The kinetics of the first-order thermal gas-phase reactions of all these compounds were investigated over 360-653K temperature range. The values of the Arrhenius logA and energy of activation of these ylides averaged 11.52±0.34s -1 and 133.20±3.14kJmol-1, respectively. The products of sealed-tube (static) and FVP were analyzed and compared. A mechanism is proposed to account for the products of reaction. The rate constants [k (s-1)] of the substrates at 500K were calculated and used to substantiate the proposed mechanism of pyrolysis, and to rationalize the thermal gas-phase reactivities of the ylides under study.
A convenient synthesis of ketenimines from thioamides with haloiminium salts
Shimizu, Masao,Gama, Yasuo,Takagi, Toshiyuki,Shibakami, Motonari,Shibuya, Isao
, p. 517 - 520 (2007/10/03)
Ketenimines were conveniently synthesized from N-monosubstituted thioacetamides with dehydrating agents such as 2-chloro-1,3- dimethylimidazolinium chloride or 2-chloro-1-methylpyridinium iodide.
Flash-vacuum Pyrolysis of N-Vinylbenzotriazoles: Formation of N-Phenylketenimines
Maquestiau, Andre,Beugnies, Didier,Flammang, Robert,Katritzky, Alan R.,Soleiman, Mohammed,at al.
, p. 1071 - 1076 (2007/10/02)
A real time analysis of the flash-vacuum pyrolysis products of 1-vinyl-, 1-(2-methylprop-1-enyl)-, and 1-styryl-benzotriazole (3), (16), and (18) has been performed by tandem mass spectrometry.In the 500-700 deg C temperature range, these compounds lose nitrogen yielding the N-phenylketenimines (14), (17), and (19), respectively.At higher pyrolysis temperatures (3) gives indole (4) via isomerization of (14), whereas from (16) the secondary products of (17) are benzene and methacrylonitrile.In a preparative pyrolysis of (18) at 800 deg C 2- and 3-phenylindole (9) and (10) respectively, have also been detected.
Rapid Acid-catalysed and Uncatalysed Hydration of Ketenimines
McCarthy, Daniel G.,Hegarty, Anthony F.
, p. 579 - 591 (2007/10/02)
The rates of hydration of a series of ketenimines (9) have been examined in water (μ 1.0; 25 deg) over the pH range 2-13.Three mechanisms of hydration to the amides (8) were noted: (a) general acid catalysis by proton transfer from H3O(1+) in the pH range 2-7 (giving kH3O(1+)/kD3O(1+) 2.65); (b) general acid catalysis by H2O at pH > 7 (where kH2O/kD2O = 4.8); (c) rate determining HO(1-) attack.The last mechanism was only shown by N-arylketenimines, e.g. (9e); other N-alkylketenimines continue to react by rate-determining proton transfer from water even at pH 13.This result is confirmed by the incorporation of just one deuterium when (9a) reacted in acidic or basic D2O, while the deuteriated ketenimine (9f) does not loose the label on the reaction in water.Substituent effects are parallel for reactions involving H(1+) transfer from H3O(1+) or H2O; the major effects are obtained on changing substituents at carbon (the protonation site).For example, replacement of C-H by C-Me reduces the reactivity by 10-20-fold, while replacement of C-Me by C-Ph reduces the rate of hydration by >100-fold.Ammonium ions also generally react with ketenimines by rate-determining H(1+) transfer to the ketenimine followed by trapping of the nitrilium ion formed by the free amine.Only with the strongest amine base studied (piperidine) does direct nucleophilic attack on the ketenimine compete.
Selectivity in Ketenimine-Thioketone Cycloadditions. 1. 1,4- and 1,2-Addition Pathways and the Synthesis of 4H-3,1-Benzothiazines, 2-Iminothietanes, and Thioacrylamides
Dondoni, Alessandro,Battaglia, Arturo,Giorgianni, Patrizia
, p. 3766 - 3773 (2007/10/02)
The cycloadditions of thiobenzophenones to ketenimines take place at different sites of the cumulene depending on the extent of substitution and the nature of the substituents.C,C-Disubstituted ketenimines whose nitrogen bears an alkyl or an ortho,ortho'-
