Nucleophilic addition to the double bond of 2,4,6-trinitrostyrene and transformations of adducts

Conditions were found under which 2,4,6-trinitrostyrene derived from 2,4,6-trinitrotoluene adds nucleophiles (thiophenol, aniline, and aliphatic amines) at the vinyl fragment to form the corresponding β-X-ethyl-2,4,6- trinitrobenzenes (X = PhS, PhNH, or R2N). In the reactions with primary aromatic amines, the initially formed adducts undergo intramolecular replacement of the nitro group followed by aromatization of the indolines that formed to the corresponding N-substituted 4,6-dinitroindoles.