69751-73-1Relevant academic research and scientific papers
Mechanism of formation of 2,1-benzisoxazoles in reactions of nitroarenes with arylacetonitriles
Orlov,Kotov,Tsivov,Rusakov
, p. 245 - 252 (2015/04/14)
Main regularities in reactions of arylacetonitriles with nitroarenes were discussed. The reaction mechanism has been suggested proceeding from the experimental data and the quantum chemical modeling of the limiting stage, the formation of the 2,1-benzisoxazole ring.
Nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion
Orlov,Sokovikov,Kotov
, p. 100 - 103 (2007/10/03)
The kinetic relations holding in nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion suggest a complex reaction mechanism involving two alternative pathways. The direction of the process is determined by the structure of intermediate σ-complex.
Nucleophilic substitution of hydrogen in activated nitroarenes by phenylacetonitrile carbanion
Orlov,Sokovikov,Kotov,Starikov
, p. 1735 - 1738 (2007/10/03)
General relations holding in nucleophilic substitution of hydrogen in para-substituted nitroarenes by phenylacetonitrile carbanion were analyzed in terms of the Klopman reactivity indices. Requirements to the substrate structure were determined, which restrict the scope of application of this method to synthesis of 2,1-benzisoxazole derivatives.
Substituent Effect on the Reaction Rate of para-Substituted Nitrobenzenes with Phenylacetonitrile
Orlov,Kotov,Rusakov,Bystryakova,Kopeikin,Mironov
, p. 538 - 540 (2007/10/03)
The substituent effect on the reaction rate of para-substituted nitrobenzenes with the phenylacetonitrile was evaluated using the model of orbital interactions. The limiting step of the reaction was presumed to have associative character.
FUNCTIONALIZATION OF AROMATIC COMPOUNDS BY NUCLEOPHILIC SUBSTITUTION OF A HYDROGEN ATOM BY THE PHENYLACETONITRILE CARBANION
Orlov, V. Yu.,Kotov, A. D.,Bystryakova, E. B.,Kopeikin, V. V.,Mironov, G. S.
, p. 1481 - 1484 (2007/10/02)
Aromatic nitro compounds containing a substituent at the para react with phenylacetonitrile in an alcohol solution of alkali with the formation of 2,1-benzisoxazoles.The CH3, NH2, OH, and certain other substituents prevent the reaction.In the reaction of benzonitrile and phthalonitrile with phenylacetonitrile in the sodium hydroxide-DMSO system substitution of a hydrogen atom at the ortho position to the nitrile group is observed; the products from substitution of a hydrogen atom were not obtained in the reaction of phenylacetonitrile with aromatic nitriles containing other substituents.
