Preparation of N-aryl-S,S-diphenylsulfilimines by nucleophilic attack of N-lithio-S,S-diphenylsulfilimine on aromatic compounds

N-Aryl-S,S-diphenylsulfilimines with unusual substitution patterns have bee n prepared by reacting the novel nitrogen nucleophile N-lithio-S,S-diphenyl sulfilimine with a range of activated aromatic substrates. N-Lithio-S,S-dip henylsulfilimine is not only able to displace chloro groups in conventional aromatic nucleophilic substitution reactions, but also, unlike S,S-dipheny lsulfilimine itself, can attack at hydrogen-bearing positions in 'vicarious ' aromatic nucleophilic substitutions of hydrogen. Crown copyright (C) 1999 Published by Elsevier Science Ltd. All rights reserved.