86981-07-9Relevant academic research and scientific papers
Nucleophilic substitution process
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, (2008/06/13)
Halonitroarylacetonitriles are prepared by reacting a halonitroaromatic compound wherein the halo substituent has an atomic number of at least 17 with an alpha,alpha-disubstituted acetonitrile in an inert solvent and in the presence of a base so that the nitrile undergoes a nucleophilic substitution on an unsubstituted ring carbon of the halonitroaromatic compound during which an alpha-substituent functions as a leaving group. The halonitroarylacetonitriles formed by the process can be readily converted into derivatives, such as pharmaceuticals.
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.
