ChemInform Abstract: 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 been prepared by reacting the novel nitrogen nucleophile N-lithio-S,S-diphenylsulfilimine with a range of activated aromatic substrates. N-Lithio-S,S-diphenylsulfilimine is not only able to displace chloro groups in conventional aromatic nucleophilic substitution reactions, but also, unlike S,S-diphenylsulfilimine itself, can attack at hydrogen-bearing positions in ‘vicarious’ aromatic nucleophilic substitutions of hydrogen.