1,3‐Dinitro‐2‐chloro‐5‐trifluorotoluene and its bridged derivatives I. An investigation on the displacement reactions of bidentate nucleophiles towards aromatic rings

Abstract

The reactions of 1,3‐dinitro‐2‐chloro‐5‐trifluorotoluene (DNCTT) (1) and its bridged compounds with bidentate nucleophiles have been investigated. Primary or secondary diamines and diethylene glycol react with 1 and its bridged derivatives by replacing the substituent group para to CF3, whereas ethanedithiol reacts either by replacing the substituent group para to CF3 or by displacing both groups and a nitro group. The results have been rationalized in terms of electronic effects and nucleophilicity of the nucleophiles.

Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

“…In each case, the product precipitated from the reaction mixture as a white amorphous solid. Compounds 6, 10, and 11 were also accessible in a single step using an adaptation of a previously published procedure, 37 as shown in Scheme 2. Treatment of 1,3-dinitro-2-chloro-5trifluoromethylbenzene 35 with the appropriate diamine 36a−c in the presence of triethylamine at 10 °C afforded the desired target molecules 6, 10, and 11 in 68−87% yield.…”