Nucleophilic substitution in dibenz[b,d]iodolium and 11,12-dihydro-10H-dibenz[b,g]iodocinium cations

Article abstract of DOI:10.1007/BF02290735

Treatment of dibenz[b,d]iodolium tetrafluoroborate with NO₂^-, Br^-, and N₃^- ions gave, along with nucleophilic substitution products, 2-nitro-, 2-bromo-, and 2-azido-2′-iodiphenyls, diphenyl, 2-iododiphenyl, and 2,2′-diiododiphenyl (products of one electron reduction), whereas 11,12-dihydro-10H-dibenz[b,g]-iododnium tetrafluoroborate underwent nucleophilic substitution with all three nucleophiles to give a single product in each case: 1-(2-nitrophenyl)-, 1-(2-bromophenyl)-, or 1-(2-azidophenyl)-3-(2-iodophenyl)propane. 1998 Plenum Publishing Corporation.