Electrophilic thallation of diphenylamine, diphenylmethylamine, triphenylamine, pyrrole, N-methylpyrrole, and pyrazole with [PhTlIII(18-crown-6)] (ClO4) (1) gives compounds of the type [PhArTlIII(18-crown-6)](ClO4) (Ar = aryl = 4′-(phenylamino)phenyl, 4′-(methylphenylamino)phenyl, 4′-(diphenylamino)phenyl, 2′-pyrrolyl, 2′-N-methylpyrrolyl, and 4′-pyrazolyl, respectively). On the other hand, the reaction of 1 with imidazole resulted in coordination of imidazole nitrogen to the thallium ion without substitution at the ring. The character of Tl-C bonds formed by the thallation is discussed on the basis of spin-spin coupling constants between thallium nucleus and ortho protons of the phenyl group, 3JTlH2.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry