Preparation and X-ray structural study of dibenziodolium derivatives

Research output: Contribution to journalArticle

17 Citations (Scopus)

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

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this