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The reactions of 1,3-dinitro-2-chloro-5-trifluorotoluene(DNCTT)(1)and its bridged com-pounds with bidentate nucleophiles have been investigated.Primary or secondary diamines anddiethylene glycol react with 1 and its bridged derivatives by replacing the substituent grouppara to CF_3,whereas ethanedithiol reacts either by replacing the substituent group para to CF_3 or by displacingboth groups and a nitro group.The results have been rationalized in terms of electronic effects andnucleophilicity of the nucleophiles.