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Synthesis 1993; 1993(12): 1215-1217
DOI: 10.1055/s-1993-35863
short paper
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Direct Isocyanomethylation of Nitroarenes via the Vicarious Nucleophilic Substitution of Hydrogen with Phenylthiomethyl Isocyanide Carbanion

Mieczysław Makosza* , Andrzej Kinowski, Stanisław Ostrowski
  • *Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, Poland
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Publication Date:
29 April 2002 (online)

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Reaction of nitroarenes with phenylthiomethyl isocyanide in the presence of potassium tert-butoxide results in the introduction of the isocyanomethyl substituent into positions ortho or para to the nitro group. The products of the reaction when subjected to mild hydrolysis can be converted into nitrobenzylic amines or their formyl derivatives.