| Abstract: | The nucleophilic aromatic substitution of N-tert-butyl-2,4,6-trinitrobenzamide (NtBB) has been carried out in dimethylsulfoxide in the presence and absence of sodium cholate under photolytic and nonphotolytic conditions. The formation of at least two free radicals was observed in the formation and decomposition of the intermediate 1-hydroxy sigma-(or Meisenheimer-)complex(es) of NtBB in the absence of oxygen. The obtained results are compared and contrasted with those for other nucleophilic aromatic substitutions in which free radicals have been observed. |