The unusual reactivity of the mono- and bis- N-(trifluoromethylsulfonyl)-substituted azaanalogs of arenesulfonochlorides

Article abstract of DOI:10.1016/S0040-4020(01)81341-7

The reactions of N-(trifluoromethylsulfonyl)arenesulfonimidoyl- and N,N′-bis (trifluoromethylsulfonyl)arenesulfonodiimidoyl chlorides of general formulas Ar - S(O) (=NSO₂CF₃)Cl (1) and Ar - S(=NSO₂CF₃)₂Cl (2) with ammonia have been investigated and found to yield the ammonium salts of [N-(trifluoromethylsulfonyl)arenesulfinyliminol-N′- (trifluoromethylsulfonyl)amides. The high oxidative ability of the chlorides (1,2) have been shown. Thus, chlorides (2) react with benzene or trifluoromethylbenzene, to form the chlorobenzene or 3-chloro-trifluoromethylbenzene. The fluorides of the general formulas Ar - S(O) (=NSO₂CF₃)F and Ar - S(=NSO₂CF₃)₂F have been prepared. Their interaction with ammonia leads to the usual formation of corresponding amides. The electron nature of new electron withdrawing substituents have been investigated.