Nucleophilic Aromatic Substitution

Abstract

A chlorogermabenzene has been generated by reaction of an aluminacyclohexadiene with germanium chloride. The cyanodemethoxylation of arenes has been accomplished using a highly oxidizing acridinium photoredox catalyst with acetone cyanohydrin as the source of cyanide. Arenediazonium triflates have been synthesized by diazotization of anilines with t -butylnitrite in the presence of trifluoromethanesulfonic acid. The detection of 2,4,6-trinitrotoluene remains an active area of research, with most methods relying on its interaction with amino groups. Likely modes of interaction include Meisenheimer complex formation and anion formation by transfer of a methyl proton. It has been shown that 1,2-azaborine, the boron–nitrogen equivalent of ortho -benzyne, has a super-electrophilic boron centre and will form adducts with xenon and with carbon monoxides under matrix isolation conditions. Nucleophilic attack of chlorine ions on benzyne gives anions that may be trapped with carbon dioxide to form the ortho-chlorobenzoate ion.