THE REACTIONS OF PHENYL(B-CARBORANYL)IODONIUM SALTS WITH NUCLEOPHILES

Article abstract of DOI:10.1016/0022-328X(85)87326-5

The reactions of phenyl(9-o-carboranyl)-, phenyl(9-m-carboranyl)- and phenyl(2-p-carboranyl)-iodonium salts with the nucleophiles F^-, Cl^-, Br^-, OH^-, C5H5N, Hg and CN^- were studied.Depending on the nature of the nucleophile and the carborane ligand in each iodonium compound, these reactions either proceed as nucleophilic substitution or via a radical mechanism.Nucleophilic substitution, which takes place at the boron atom, of the carborane nucleus only, gives carboranylation products of nucleophiles.Free-radical processes are characterized by braking of the C-I⁺ bonds with the formation of phenyl radicals and their transformation products.The reasons for such an unusual behaviour of phenyl(B-carboranyl)iodonium salts in reactions with nucleophilic agents are discussed in the light of the results obtained and previous results.