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

Article abstract of DOI:10.1016/S0040-4020(99)00550-5

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.