77158-79-3Relevant academic research and scientific papers
Specific ortho-Cyanomethylation of Nitroarenes via the Vicarious Nucleophilic Substitution of Hydrogen
Makosza, Mieczyslaw,Wenaell, Maria,Golinski, Miroslaw,Kinowski, Andrzej
, p. 427 - 432 (2007/10/02)
The vicarious nucleophilic substitution of hydrogen in nitroarenes with acetonitrile derivatives XCH2CN in t-BuOK/THF base/solvent system proceeds exclusively ortho to the nitro group.Strong influence of substituents Z in 3-Z-nitrobenzene derivatives on the orientation has been observed.
Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with Carbanions of α-Haloalkyl Phenyl Sulfones
Makosza, Mieczyslaw,Golinski, Jerzy,Baran, Janusz
, p. 1488 - 1494 (2007/10/02)
Carbanions of α-chloroalkyl phenyl sulfones and N,N-dialkyl-α-chloroalkanesulfonamides react with nitrobenzenes to effect direct nucleophilic replacement of hydrogen ortho and para to the nitro group, with vicarious loss of chloride anion, to give the corresponding nitrobenzylsulfonyl derivatives.The reaction occurs much more rapidly than the replacement of such good leaving groups as halogen, methoxy, and phenoxy.Most substituents in the nitrobenzene ring do not interfere with the reaction.The effect of substituents in the nitrobenzene and the carbanion on the orientation of the substitution is discussed.
Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with α-Substituted Nitriles and Esters. Direct α-Cyanoalkylation and α-Carbalkoxyalkylation of Nitroarenes
Makosza, Mieczyslaw,Winiarski, Jerzy
, p. 1494 - 1499 (2007/10/02)
Carbanions generated from alkanenitriles bearing α-chloro, α-OR, or α-SR groups and from aliphatic esters bearing α-SR groups react with mononitroarenes to replace hydrogen atoms of the nitroaromatic ring ortho or para to the nitro group with α-cyanoalkyl or α-carbalkoxyalkyl substituents.The nucleophilic replacement of hydrogen with such carbanions proceeds faster than substitution of halogen ortho or para to the nitro group.
