Mechanism of formation of 2,1-benzisoxazoles in reactions of nitroarenes with arylacetonitriles
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.
Orlov,Kotov,Tsivov,Rusakov
p. 245 - 252
(2015/04/14)
FUNCTIONALIZATION OF AROMATIC COMPOUNDS BY NUCLEOPHILIC SUBSTITUTION OF A HYDROGEN ATOM BY THE PHENYLACETONITRILE CARBANION
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.
Orlov, V. Yu.,Kotov, A. D.,Bystryakova, E. B.,Kopeikin, V. V.,Mironov, G. S.
p. 1481 - 1484
(2007/10/02)
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