Electrophilic Thallation of Aniline Derivatives and Nitrogen Heterocycles with Phenylthallium(III) 18-Crown-6 Diperchlorate

Fumitoshi Kakiuchi, Kouichi Ohe, Naoto Chatani, Hideo Kurosawa, Shinji Murai, Yoshikane Kawasaki

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)752-756
Number of pages5
JournalOrganometallics
Volume11
Issue number2
DOIs
Publication statusPublished - 1992 Feb 1
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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