Electrophilic Thallation of Phenol and Its Derivatives with Phenylthalllum(III) Crown Ether Complexes

Fumitoshi Kakiuchi, Yoshikane Kawasaki, Norihide Enomoto, Hiroshi Akita, Kouichi Ohe, Naoto Chatani, Hideo Kurosawa, Shinji Murai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reaction of [phenylthallium(III)(18-crown-6)] diperchlorate, [PhTlIII(18-crown-6)](Cl04)2 (1a), with phenol gives [phenyl(4′-hydroxyphenyl)thallium(III)(18-crown-6)] Perchlorate (2), the phenolic OH having remained intact. The complex la reacts also with alkylphenols, methoxyphenols, catechol, resorcinol, and pyrogallol to give thallated products exclusively at trie para position of the electron-donating group (OH or OCH3) without suffering from reduction of thallium (III). No reaction takes place with benzene, toluene, and tert-butylbenzene.

Original languageEnglish
Pages (from-to)2056-2060
Number of pages5
JournalOrganometallics
Volume10
Issue number6
DOIs
Publication statusPublished - 1991 Jun 1
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Kakiuchi, F., Kawasaki, Y., Enomoto, N., Akita, H., Ohe, K., Chatani, N., Kurosawa, H., & Murai, S. (1991). Electrophilic Thallation of Phenol and Its Derivatives with Phenylthalllum(III) Crown Ether Complexes. Organometallics, 10(6), 2056-2060. https://doi.org/10.1021/om00052a063