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1,3‐Dinitro‐2‐chloro‐5‐trifluorotoluene and its bridged derivatives I. An investigation on the displacement reactions of bidentate nucleophiles towards aromatic rings
Author(s) -
Ji JingShun,
Chen MeiJin,
Wang QiWen,
Sheng Wei
Publication year - 1991
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19910090409
Subject(s) - chemistry , nucleophile , substituent , nitro , denticity , medicinal chemistry , group (periodic table) , diethylene glycol , ring (chemistry) , stereochemistry , organic chemistry , ethylene glycol , crystal structure , catalysis , alkyl
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 CF 3 , whereas ethanedithiol reacts either by replacing the substituent group para to CF 3 or by displacing both groups and a nitro group. The results have been rationalized in terms of electronic effects and nucleophilicity of the nucleophiles.