Unusual oxidative cleavage of the aryl-ethynyl bonds in (arylethynyl)polymethylbenzenes with iodine in dimethyl sulfoxide

M. S. Yusubov, G. A. Zholobova, I. L. Filimonova, V. P. Vasil'eva, V. D. Filimonov, Ki Whan Chi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

While heating 1,2,4,5-tetramethyl-3,6-bis(phenylethynyl)benzene, 1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene, and 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene with iodine in DMSO in the absence of oxygen, the triple bonds are oxidized to give the corresponding 1,2-diketones. In the presence of oxygen, the previously unknown competitive oxidative process causes the cleavage of the aryl-ethynyl bonds so that duroquinone and the corresponding 4-hydroxybenzils are formed. This cleavage is produced by oxygen only in the presence of iodine and DMSO. It was shown that the key stage of the process is the formation of intermediate charge-transfer complexes between polymethylbenzene rings and iodine.

Original languageEnglish
Pages (from-to)1051-1055
Number of pages5
JournalRussian Chemical Bulletin
Volume50
Issue number6
DOIs
Publication statusPublished - 2001

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Dimethyl Sulfoxide
Benzene
Iodine
Oxygen
Charge transfer
Heating

Keywords

  • 1,2-diketones
  • Alkynes
  • Dimethyl sulfoxide
  • Iodine
  • Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Unusual oxidative cleavage of the aryl-ethynyl bonds in (arylethynyl)polymethylbenzenes with iodine in dimethyl sulfoxide. / Yusubov, M. S.; Zholobova, G. A.; Filimonova, I. L.; Vasil'eva, V. P.; Filimonov, V. D.; Chi, Ki Whan.

In: Russian Chemical Bulletin, Vol. 50, No. 6, 2001, p. 1051-1055.

Research output: Contribution to journalArticle

Yusubov, M. S. ; Zholobova, G. A. ; Filimonova, I. L. ; Vasil'eva, V. P. ; Filimonov, V. D. ; Chi, Ki Whan. / Unusual oxidative cleavage of the aryl-ethynyl bonds in (arylethynyl)polymethylbenzenes with iodine in dimethyl sulfoxide. In: Russian Chemical Bulletin. 2001 ; Vol. 50, No. 6. pp. 1051-1055.
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AU - Yusubov, M. S.

AU - Zholobova, G. A.

AU - Filimonova, I. L.

AU - Vasil'eva, V. P.

AU - Filimonov, V. D.

AU - Chi, Ki Whan

PY - 2001

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AB - While heating 1,2,4,5-tetramethyl-3,6-bis(phenylethynyl)benzene, 1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene, and 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene with iodine in DMSO in the absence of oxygen, the triple bonds are oxidized to give the corresponding 1,2-diketones. In the presence of oxygen, the previously unknown competitive oxidative process causes the cleavage of the aryl-ethynyl bonds so that duroquinone and the corresponding 4-hydroxybenzils are formed. This cleavage is produced by oxygen only in the presence of iodine and DMSO. It was shown that the key stage of the process is the formation of intermediate charge-transfer complexes between polymethylbenzene rings and iodine.

KW - 1,2-diketones

KW - Alkynes

KW - Dimethyl sulfoxide

KW - Iodine

KW - Oxidation

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