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 language | English |
|---|---|
| Pages (from-to) | 1051-1055 |
| Number of pages | 5 |
| Journal | Russian Chemical Bulletin |
| Volume | 50 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2001 |
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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 journal › Article
}
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
UR - http://www.scopus.com/inward/record.url?scp=0035539764&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035539764&partnerID=8YFLogxK
U2 - 10.1023/A:1011329621330
DO - 10.1023/A:1011329621330
M3 - Article
AN - SCOPUS:0035539764
VL - 50
SP - 1051
EP - 1055
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 1066-5285
IS - 6
ER -