Preparation and X-ray structural study of dibenziodolium derivatives

Pavel S. Postnikov, Olga A. Guselnikova, Mekhman S. Yusubov, Akira Yoshimura, Victor N. Nemykin, Viktor Zhdankin

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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 (US)
Pages (from-to)5783-5788
Number of pages6
JournalJournal of Organic Chemistry
Issue number11
StatePublished - Jun 5 2015

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© 2015 American Chemical Society.


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