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

研究成果: Article › 査読

7 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2056-2060
ページ数	5
ジャーナル	Organometallics
巻	10
号	6
DOI	https://doi.org/10.1021/om00052a063
出版ステータス	Published - 1991 6月 1
外部発表	はい

ASJC Scopus subject areas

物理化学および理論化学
有機化学
無機化学

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10.1021/om00052a063

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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,

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doi = "10.1021/om00052a063",

language = "English",

volume = "10",

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journal = "Organometallics",

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publisher = "American Chemical Society",

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

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