Generation of electrophilic iodine from iodine monochloride in neutral media. Iodination and protodeiodination of carbazole

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Abstract

In reaction of iodine monochloride with CF3COOAg, CH 3COONa or (CH3COO)2Pb in acetonitrile and acetic acid the chloride is bonded by metal cations, and electrophilic iodine is generated able to easily iodinate anthracene and carbazole. However at the iodination of anthracene in the presence of oxygen the prevailing process is anthracene oxidation to anthraquinone. In the presence of sulfuric acid protodeiodination of 3-iodocarbazole was found to occur resulting in rearranged products.

Original languageEnglish
Pages (from-to)875-880
Number of pages6
JournalRussian Journal of Organic Chemistry
Volume39
Issue number6
DOIs
Publication statusPublished - 1 Jun 2003

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Iodine
Anthraquinones
Acetic Acid
Cations
Chlorides
Metals
Oxygen
Oxidation
iodine monochloride
carbazole
anthracene
acetonitrile
sulfuric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "In reaction of iodine monochloride with CF3COOAg, CH 3COONa or (CH3COO)2Pb in acetonitrile and acetic acid the chloride is bonded by metal cations, and electrophilic iodine is generated able to easily iodinate anthracene and carbazole. However at the iodination of anthracene in the presence of oxygen the prevailing process is anthracene oxidation to anthraquinone. In the presence of sulfuric acid protodeiodination of 3-iodocarbazole was found to occur resulting in rearranged products.",
author = "Filimonov, {V. D.} and Krasnokutskaya, {E. A.} and Lesina, {Yu A.}",
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T1 - Generation of electrophilic iodine from iodine monochloride in neutral media. Iodination and protodeiodination of carbazole

AU - Filimonov, V. D.

AU - Krasnokutskaya, E. A.

AU - Lesina, Yu A.

PY - 2003/6/1

Y1 - 2003/6/1

N2 - In reaction of iodine monochloride with CF3COOAg, CH 3COONa or (CH3COO)2Pb in acetonitrile and acetic acid the chloride is bonded by metal cations, and electrophilic iodine is generated able to easily iodinate anthracene and carbazole. However at the iodination of anthracene in the presence of oxygen the prevailing process is anthracene oxidation to anthraquinone. In the presence of sulfuric acid protodeiodination of 3-iodocarbazole was found to occur resulting in rearranged products.

AB - In reaction of iodine monochloride with CF3COOAg, CH 3COONa or (CH3COO)2Pb in acetonitrile and acetic acid the chloride is bonded by metal cations, and electrophilic iodine is generated able to easily iodinate anthracene and carbazole. However at the iodination of anthracene in the presence of oxygen the prevailing process is anthracene oxidation to anthraquinone. In the presence of sulfuric acid protodeiodination of 3-iodocarbazole was found to occur resulting in rearranged products.

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