That 4-chloro-l, 3-phenylenediamine (23) undergoes reaction with potassium phenyl thiolate is of interest in that this should be a particularly disfavored substrate for nucleophilic aromatic substitution. A number of other aniline substrates (4-chloroaniline and 2, 4-, 3, 4-, and 3, 5-dichloroaniline) afforded mixtures upon prolonged exposure to potassium phenyl thiolate from which we were unable to obtain product (pheny1thio) anilines in rigorously ...
