Search

p -Phenylenediamine reacts with Sanger's reagent in hot ethanol to give the expected mono- and di-substitution products, but in ethanol at room temperature, it gave exclusively 2-nitro-5-fluorophenyl- p -phenylenediamine, where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p -phenylenediamine and aniline with Sanger's reagent were compared in the cheap, 'green' solvent ethanol. An unexpected product forms from reacting Sanger's reagent with p -phenylenediamine [ABSTRACT FROM AUTHOR]

2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride. [ABSTRACT FROM AUTHOR]