Electrophilic thallation of phenol and its derivatives with phenylthallium(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)](ClO4)2 (1a), with phenol gives [phenyl(4′-hydroxyphenyl)thallium(III)(18-crown-6)] perchlorate (2), the phenolic OH having remained intact. The complex 1a reacts also with alkylphenols, methoxyphenols, catechol, resorcinol, and pyrogallol to give thallated products exclusively at the 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
Publication statusPublished - 1991
Externally publishedYes

Fingerprint

Crown Ethers
thallium
Phenol
phenols
ethers
Thallium
Derivatives
perchlorates
Pyrogallol
toluene
benzene
Toluene
Benzene
products
electrons
Electrons
18-crown-6
perchlorate

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Kakiuchi, F., Kawasaki, Y., Enomoto, N., Akita, H., Ohe, K., Chatani, N., ... Murai, S. (1991). Electrophilic thallation of phenol and its derivatives with phenylthallium(III) crown ether complexes. Organometallics, 10(6), 2056-2060.

Electrophilic thallation of phenol and its derivatives with phenylthallium(III) crown ether complexes. / Kakiuchi, Fumitoshi; Kawasaki, Yoshikane; Enomoto, Norihide; Akita, Hiroshi; Ohe, Kouichi; Chatani, Naoto; Kurosawa, Hideo; Murai, Shinji.

In: Organometallics, Vol. 10, No. 6, 1991, p. 2056-2060.

Research output: Contribution to journalArticle

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 phenylthallium(III) crown ether complexes', Organometallics, vol. 10, no. 6, pp. 2056-2060.
Kakiuchi, Fumitoshi ; Kawasaki, Yoshikane ; Enomoto, Norihide ; Akita, Hiroshi ; Ohe, Kouichi ; Chatani, Naoto ; Kurosawa, Hideo ; Murai, Shinji. / Electrophilic thallation of phenol and its derivatives with phenylthallium(III) crown ether complexes. In: Organometallics. 1991 ; Vol. 10, No. 6. pp. 2056-2060.
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AU - Ohe, Kouichi

AU - Chatani, Naoto

AU - Kurosawa, Hideo

AU - Murai, Shinji

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