3122-21-2Relevant articles and documents
Synthesis of 2-Cyano-1,1,2,2-tetraphenylethyl Cation and Silver Ion Assisted Solvolysis of sym-Tetraphenylethylene Dichloride
Wo, Shiming,Zieger, Herman E.,Millar, Michelle M.,Koch, Stephen A.
, p. 5925 - 5930 (1995)
The reaction of 3-chloro-2,2,3,3-tetraphenylpropanenitrile (2) with AgSbF6 or SbCl5 below -55 deg C in methylene chloride produces the stable, long-lived cation 2-cyano-1,1,2,2-tetraphenylethyl cation (5).Treatment of 5 with TMSCN affords a 98percent yield of 2,2,3,3-tetraphenylsuccinonitrile.It was also found that cation 5 generated with AlCl3 at 0 deg C can undergo intramolecular aromatic substitution to give 9-(cyanodiphenylmethyl)fluorene (8).In the reactions of sym-tetraphenylethylene dichloride (1) with CF3COOAg in the presence of methanol, it was found that tetraphenylethanone dimethyl ketal (9) can be synthesized in 91percent yield.Because rearrangement occured, 1-methoxy-1,2,2,2-tetraphenylethyl cation (15) is proposed as a reaction intermediate.In contrast, treatment of dichloride 1 with CF3CO2Ag in the presence of phenol or isopropyl or allyl alcohol did not produce the corresponding ketals but the 1,3-dioxolane ortho esters 19, 20, or 21 (2-alkoxy-2-trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolanes).
Conformations of 1,2-dicyano-1,1,2,2-tetraphenylethane and cyanodiphenylmethyl peroxide
Lam, Yulin,Lee, Gene-Hsiang,Liang, Eping
, p. 1033 - 1034 (2001)
The solid-state structures of 1,2-dicyano-1,1,2,2-tetraphenylethane and cyanodiphenylmethyl peroxide are determined by X-ray crystallography. Both molecules adopt the trans conformation in the solid-state. Experimentally derived values of the energy diffe
Synthesis of Succinonitrile Derivatives by Homocoupling from Cyanohydrin Derivatives with a Low-Valent Titanium Reagent
Endo, Ryusei,Kishida, Atsushi,Matsunaga, Kazuma,Nagasawa, Kokoro,Takatori, Kazuhiko
, (2022/02/07)
A method is described for synthesizing succinonitrile derivatives bearing alkyl or aryl substituents from cyanohydrin derivatives using low-valent titanium. The active species in this reaction is proposed to be a resonance hybrid of the TiIV nitrile enolate and TiIII alkyl radical.
Electrocatalytic dimerization of diarylacetonitriles mediated by sodium halides
Elinson, Michail N.,Ilovaisky, Alexey I.,Merkulova, Valentina M.,Zaimovskaya, Tatiana A.,Belyakov, Pavel A.,Nikishin, Gennady I.
body text, p. 207 - 208 (2011/03/19)
A new electrocatalytic reaction affording tetraarylsuccinonitriles in 80-100% yields by the oxidation of diarylacetonitriles in an undivided cell with sodium halides as mediators is described.
THERMALLY MODULATED ANTIOXIDANTS
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Page/Page column 49; 51, (2008/06/13)
Most carbon-centered free radical antioxidants are generated through hydrogen abstraction. Disclosed herein are a new class of antioxidant precursor compounds of the formula A-B, wherein upon exposure of the compounds to an increase in temperature, the co
Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals
Frenette, Mathieu,Aliaga, Carolina,Font-Sanchis, Enrique,Scaiano
, p. 2579 - 2582 (2007/10/03)
(Matrix Presented) The temperature dependence of the dissociation of dimers formed from highly stabilized carbon-centered radicals has been examined. Analysis of the data yields the bond dissociation energy (BDE) for the central head-to-head C-C bond in t
Selective and efficient heterogeneous hydration of nitriles to amides using silica supported manganese dioxide
Khadilkar, Bhushan M.,Madyar, Virendra R.
, p. 2814 - 2819 (2007/10/03)
A highly efficient and selective method for hydration of nitriles to amides without formation of any detectable amount of acid, under heterogeneous reaction condition using silica supported manganese dioxide is reported. The mechanism of the reaction has been discussed. The reagent preparation is easy and carried out under microwave exposure within 5 min. The silica supported MnO2 reagent has been characterized by DRIFT and XRD techniques. Quantitative yields are obtained for commercially important heterocyclic amides such as pyridinecarboxamide, nicotinamide and pyrazinamide.
Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives
Makosza, Mieczyslaw,Stalinski, Krzysztof
, p. 8797 - 8810 (2007/10/03)
Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitrobenzenes in the para position to form the corresponding σ(H)-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitution of hydrogen, ONSH or vicarious nucleophilic substitution, VNS.
Alkylation of Nitrile Anions by Tertiary α-Halo Ketones and Nitriles
Ros, Francisco,Rosa, Jose de la,Enfedaque, Juan
, p. 5419 - 5424 (2007/10/02)
Potassium salts of nitriles bearing carbethoxy, cyano, or phenyl groups at the α carbon react with tertiary α-halo ketones and nitriles (1-5) in DMSO or HMPA to provide the alkylated β-keto- or β-cyano-β,β-dialkyl nitriles 6-10 in useful yields. (PhCHCN)(-) undergoes cyclization with p-XC6H4COCCl(CH3)2 to produce 2(5H)-furanone 11.Reaction of (Ph2CCN)(-) with PhCOCCl(CH3)2 affords the hydrolyzed ketone 12a and recovered carbon acid, while the anion undergoes oxidative dimerization to NCCPh2CPh2CN with p-O2NC6H4COCCl(CH3)2 with concomitant formation of the reduced ketone p-O2NC6H4COCH(CH3)2 and the hydrolyzed ketone 12b.The alkylations of (-) and (-) with p-O2NC6H4COCX(CH3)2 take place by the SRN1 process.
