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

Результат исследований: Материалы для журналаСтатья

1 цитирование (Scopus)

Выдержка

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.

Язык оригиналаАнглийский
Страницы (с-по)1051-1055
Число страниц5
ЖурналRussian Chemical Bulletin
Том50
Номер выпуска6
DOI
СостояниеОпубликовано - 2001

Отпечаток

Dimethyl Sulfoxide
Benzene
Iodine
Oxygen
Charge transfer
Heating

ASJC Scopus subject areas

  • Chemistry(all)

Цитировать

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.

В: Russian Chemical Bulletin, Том 50, № 6, 2001, стр. 1051-1055.

Результат исследований: Материалы для журналаСтатья

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. В: Russian Chemical Bulletin. 2001 ; Том 50, № 6. стр. 1051-1055.
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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.",
keywords = "1,2-diketones, Alkynes, Dimethyl sulfoxide, Iodine, Oxidation",
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TY - JOUR

T1 - Unusual oxidative cleavage of the aryl-ethynyl bonds in (arylethynyl)polymethylbenzenes with iodine in dimethyl sulfoxide

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

Y1 - 2001

N2 - 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.

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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U2 - 10.1023/A:1011329621330

DO - 10.1023/A:1011329621330

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