Preparation and X-ray structural study of dibenziodolium derivatives

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Abstract

New experimental procedures for the preparation of dibenziodolium salts by oxidative cyclization of 2-iodobiphenyl in the presence of appropriate strong acids are described. Particularly useful is a convenient one-pot synthesis of dibenziodolium hydrogen sulfate from 2-iodobiphenyl using Oxone as an inexpensive and environmentally safe oxidant. Dibenziodolium hydrogen sulfate, bis(triflyl)imidate, or triflate can be readily converted to various other dibenziodolium derivatives (chloride, bromide, thiocyanate, azide, cyanide, phenylsulfinate) by anion exchange. Structures of key products have been established by single-crystal X-ray diffraction analysis. Particularly interesting is the X-ray structure of dibenziodolium thiocyanate, which represents the first example of a structurally characterized hypervalent iodine compound with a relatively short iodine-sulfur secondary bond distance.

Original languageEnglish
Pages (from-to)5783-5788
Number of pages6
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
Publication statusPublished - 5 Jun 2015

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Derivatives
X rays
Sulfates
Hydrogen
Iodine Compounds
Imidoesters
Azides
Cyclization
Cyanides
Bromides
Sulfur
Oxidants
Iodine
X ray diffraction analysis
Anions
Chlorides
Salts
diphenyleneiodonium
Single crystals
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Preparation and X-ray structural study of dibenziodolium derivatives",
abstract = "New experimental procedures for the preparation of dibenziodolium salts by oxidative cyclization of 2-iodobiphenyl in the presence of appropriate strong acids are described. Particularly useful is a convenient one-pot synthesis of dibenziodolium hydrogen sulfate from 2-iodobiphenyl using Oxone as an inexpensive and environmentally safe oxidant. Dibenziodolium hydrogen sulfate, bis(triflyl)imidate, or triflate can be readily converted to various other dibenziodolium derivatives (chloride, bromide, thiocyanate, azide, cyanide, phenylsulfinate) by anion exchange. Structures of key products have been established by single-crystal X-ray diffraction analysis. Particularly interesting is the X-ray structure of dibenziodolium thiocyanate, which represents the first example of a structurally characterized hypervalent iodine compound with a relatively short iodine-sulfur secondary bond distance.",
author = "Postnikov, {Pavel S.} and Olga Andreevna Guselnikova and Yusubov, {Mekhman S.} and Akira Yoshimura and Nemykin, {Victor N.} and Zhdankin, {Viktor Vladimirovich}",
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T1 - Preparation and X-ray structural study of dibenziodolium derivatives

AU - Postnikov, Pavel S.

AU - Guselnikova, Olga Andreevna

AU - Yusubov, Mekhman S.

AU - Yoshimura, Akira

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor Vladimirovich

PY - 2015/6/5

Y1 - 2015/6/5

N2 - New experimental procedures for the preparation of dibenziodolium salts by oxidative cyclization of 2-iodobiphenyl in the presence of appropriate strong acids are described. Particularly useful is a convenient one-pot synthesis of dibenziodolium hydrogen sulfate from 2-iodobiphenyl using Oxone as an inexpensive and environmentally safe oxidant. Dibenziodolium hydrogen sulfate, bis(triflyl)imidate, or triflate can be readily converted to various other dibenziodolium derivatives (chloride, bromide, thiocyanate, azide, cyanide, phenylsulfinate) by anion exchange. Structures of key products have been established by single-crystal X-ray diffraction analysis. Particularly interesting is the X-ray structure of dibenziodolium thiocyanate, which represents the first example of a structurally characterized hypervalent iodine compound with a relatively short iodine-sulfur secondary bond distance.

AB - New experimental procedures for the preparation of dibenziodolium salts by oxidative cyclization of 2-iodobiphenyl in the presence of appropriate strong acids are described. Particularly useful is a convenient one-pot synthesis of dibenziodolium hydrogen sulfate from 2-iodobiphenyl using Oxone as an inexpensive and environmentally safe oxidant. Dibenziodolium hydrogen sulfate, bis(triflyl)imidate, or triflate can be readily converted to various other dibenziodolium derivatives (chloride, bromide, thiocyanate, azide, cyanide, phenylsulfinate) by anion exchange. Structures of key products have been established by single-crystal X-ray diffraction analysis. Particularly interesting is the X-ray structure of dibenziodolium thiocyanate, which represents the first example of a structurally characterized hypervalent iodine compound with a relatively short iodine-sulfur secondary bond distance.

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