16483-45-7

Upstream product

• 140-53-4 p-chlorobenzyl cyanide 
• 104-88-1 4-chlorobenzaldehyde 
• 70777-66-1 (Z)-2,3-bis(4-chlorophenyl)acrylonitrile 
• 5909-74-0 N-phenyl-C-(4-chlorophenyl)nitrone 
• 74225-36-8 C₁₇H₁₉ClN₂OSi 
• 92686-29-8 Z-2-(4-chlorophenyl)-3-dimethylaminoacrylonitrile 

Relevant academic research and scientific papers

Stereoselective electrocatalytic oxidative coupling of phenylacetonitriles: Facile and convenient way to trans-α,β-dicyanostilbenes

Electrolysis of phenylacetonitriles in methanol in an undivided cell in the presence of sodium halides as mediators induces a stereoselective oxidative coupling process that results in the formation of trans-α,β- dicyanostilbenes in 60-85% yield with 40-70% current efficiency. The application of this efficient stereoselective electrocatalytic method to the formation of trans-α,β-dicyanostilbenes represents an environmentally benign synthetic strategy and is valuable from the viewpoint of large-scale processes. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Stereoarrayed 2,3-Disubstituted 1-Indanols via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation

Activated racemic 2,3-disubstituted 1-indanones 1 possessing two stereolabile centers were stereoselectively reduced to the corresponding chiral 2,3-disubstituted-1-indanols 2 by ruthenium(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydro

Anodic Dimerization of Enamines, 2-Cyano-2-phenylvinylamines

The effects of substituents (R1, R2, and R3) on the electrochemical oxidation of the title enamines, R1-C6H4-C(CN)=CH-NR2R3 (1) were investigated in acetonitrile at a glassy carbon electrode together with the oxidation of a related amine, Ph-CH(CN)-CH2-NMe2 (5).Cyclic voltammetry of 1 showed two or more anodic peaks depending upon the substituents.On controlled potential electrolysis at the potential of the first anodic wave, 1 with R1 = H, R2 = alkyl, and R3 = alkyl or H gave diphenylmethane derivatives in which two molecules of the starting enamine are coupled between the β-carbon atom and the phenyl ring para to the enamino group.Essentially the same results were obtained for 1 with R1 = m-Me or m-Cl and R2 = R3 = Me.A mechanism involving the dimerization of radical cations from 1 is proposed.Electrolysis of 1 with R1 = p-Cl or p-Me and R2 = R3 = Me, on the other hand, gave diphenylethane derivatives via coupling between the β-carbon atoms.No stable product was obtained from 1 with a phenyl group on the nitrogen atom.Results on electrolyses of the amine 5 and 1 with R1 = H and R2 = R3 = Me at the voltammetric peak potential of 5 argue against the possibility that an enamine is formed as an intermediate in the electrochemical dealkylation of aliphatic amines.Keywords - β-cyanoenamine; oxidative dimerization; radical cation; electrochemical oxidation; cyclic voltammetry; controlled potential electrolysis, ESR spectrum.

Reactions of Trimethylsilyl Cyanide and N-(Trimethylsilyl)diphenylmethyleneamine with Nitrones and Thermal Decompositions of Their Adducts

Trimethylsilyl cyanide (1) and N-(trimethylsilyl)diphenylmethyleneamine (2) reacted with α-aryl-N-phenylnitrones to afford the corresponding 1:1 adducts 4 and 5 respectively.Thermal decomposition of 4 in refluxing xylene gave azoxybenzene, stereoisomers of 2,3-diarylsuccinonitriles, α-aminonitriles and/or benzanilides, whose yields depended on the nature of substituents on phenyl group of 4.On heating in benzene 5 afforded a mixture of azoxybenzene and meso-N,N'-bis(diphenylmethylene)-1,2-diarylethylenediamines.On the other hand, reactions of 1 and 2 with N-(diphenylmethylene)aniline N-oxide or N-(9-fluorenylidene)aniline N-oxide did not give the corresponding 1:1 adducts, but instead compounds arising from thermal decomposition of initial 1:1 adducts were directly obtained.The reaction of 1 with N-(p-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.