1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds

V. K. Chaikovskii, V. D. Filimonov, A. A. Funk, V. I. Skorokhodov, V. D. Ogorodnikov

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

1,3-Diiodo-5,5-dimethylhydantoin in organic solvents successfully iodinates alkylbenzenes, aromatic amines, and phenyl ethers. The reactivity of electrophilic iodine is controlled by acidity of the medium. Superelectrophilic iodine generated upon dissolution of 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid readily reacts with electron-deficient arenes at 0 to 20°C with formation of the corresponding iodo derivatives in good yields. The structure of electrophilic iodine species generated from 1,3-diiodo-5,5- dimethylhydantoin in sulfuric acid is discussed.

Original languageEnglish
Pages (from-to)1291-1296
Number of pages6
JournalRussian Journal of Organic Chemistry
Volume43
Issue number9
DOIs
Publication statusPublished - Sep 2007

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Aromatic compounds
Iodine
Phenyl Ethers
Acidity
Organic solvents
Amines
Dissolution
Derivatives
Electrons
5,5-dimethylhydantoin
sulfuric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds. / Chaikovskii, V. K.; Filimonov, V. D.; Funk, A. A.; Skorokhodov, V. I.; Ogorodnikov, V. D.

In: Russian Journal of Organic Chemistry, Vol. 43, No. 9, 09.2007, p. 1291-1296.

Research output: Contribution to journalArticle

Chaikovskii, V. K. ; Filimonov, V. D. ; Funk, A. A. ; Skorokhodov, V. I. ; Ogorodnikov, V. D. / 1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds. In: Russian Journal of Organic Chemistry. 2007 ; Vol. 43, No. 9. pp. 1291-1296.
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