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

doi:10.1021/om00052a063

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 journal › Article › peer-review

7 Citations (Scopus)

Abstract

The reaction of [phenylthallium(III)(18-crown-6)] diperchlorate, [PhTl^III(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 language	English
Pages (from-to)	2056-2060
Number of pages	5
Journal	Organometallics
Volume	10
Issue number	6
DOIs	https://doi.org/10.1021/om00052a063
Publication status	Published - 1991 Jun 1
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om00052a063

Cite this

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title = "Electrophilic Thallation of Phenol and Its Derivatives with Phenylthalllum(III) Crown Ether Complexes",

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.",

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

year = "1991",

month = jun,

day = "1",

doi = "10.1021/om00052a063",

language = "English",

volume = "10",

pages = "2056--2060",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "6",

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TY - JOUR

T1 - Electrophilic Thallation of Phenol and Its Derivatives with Phenylthalllum(III) Crown Ether Complexes

AU - Kakiuchi, Fumitoshi

AU - Kawasaki, Yoshikane

AU - Enomoto, Norihide

AU - Akita, Hiroshi

AU - Ohe, Kouichi

AU - Chatani, Naoto

AU - Kurosawa, Hideo

AU - Murai, Shinji

PY - 1991/6/1

Y1 - 1991/6/1

N2 - 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.

AB - 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.

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DO - 10.1021/om00052a063

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JO - Organometallics

JF - Organometallics

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ER -

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

Abstract

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