Aromatic substitution by phenylnitrenium and naphthylnitrenium ions formed from phenyl azide and 1-azidonaphthalene in the presence of trifluoromethanesulphonic acid

Abstract

Aromatic N-substitution by phenylnitrenium ions generated from phenyl azide in the presence of a catalytic amount of trifluoromethanesulphonic acid gave diarylamines (in especially good yield in the reactions with biphenyl or naphthalene), whereas naphthylnitrenium ions from 1-azidonaphthalene react with benzene to afford a C-substitution product, 1-amino-4-phenylnaphthalene.