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Kinetics and Mechanism of the Cyclization of Methyl (2-Cyano-4,6 dinitrophenylsulfanyl)acetate Producing Methyl 3-Amino-5,7-dinitrobenzo[b]thiophene-2-carboxylate
Pešková, M., Hanusek, J. and Macháček, V. Kinetics and Mechanism of the Cyclization of Methyl (2-Cyano-4,6 dinitrophenylsulfanyl)acetate Producing Methyl 3-Amino-5,7-dinitrobenzo[b]thiophene-2-carboxylate Chemical Papers, Vol.58, No. 2, 2004, 133-138
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Attached Files |
| Name |
Description |
MIMEType |
Size |
Downloads |
n582a133.pdf
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582a133.pdf |
application/pdf |
239.38KB |
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| Author(s) |
Pešková, M.
Hanusek, J.
Macháček, V.
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| Title |
Kinetics and Mechanism of the Cyclization of Methyl (2-Cyano-4,6 dinitrophenylsulfanyl)acetate Producing Methyl 3-Amino-5,7-dinitrobenzo[b]thiophene-2-carboxylate
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| Journal name |
Chemical Papers
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| Publication date |
2004
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| Year available |
2004
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| Volume number |
58
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| Issue number |
2
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| ISSN |
0366-6352
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| Start page |
133
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| End page |
138
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2004
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| Abstract/Summary |
Base-catalyzed ring closure of methyl (2-cyano-4,6-dinitrophenylsulfanyl)acetate produces methyl 3-amino-5,7-dinitrobenzo[b]thiophene-2-carboxylate. This means that the carbanion initially formed attacks cyano group and not nitro group. The kinetics of this cyclization reaction has been studied in methanolic buffers of tert-amine/tert-ammonium chloride, and the reaction mechanism was suggested. The reaction is subject to general base catalysis. The found value of the Brønsted coefficient is β = 0.9 ± 0.1, which indicates a late transition state of the rate-limiting proton transfer.
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