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Reactions of 2-unsubstituted 1H-Imidazole 3-Oxides with 2,2- Bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A stepwise 1,3-dipolar Cycloaddition


Mloston, G; Jasinski, M; Linden, A; Heimgartner, H (2006). Reactions of 2-unsubstituted 1H-Imidazole 3-Oxides with 2,2- Bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A stepwise 1,3-dipolar Cycloaddition. Helvetica Chimica Acta, 89(7):1304-1316.

Abstract

The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-
2H-imidazol-2-ylidene)malononitriles 11, respectively, depending on the solvent used. In one example, a 1 : 1 complex, 12, of the 1H-imidazole 3-oxide and hexafluoroacetone hydrate was isolated as a second product. The formation of the products is explained by a stepwise 1,3-dipolar cycloaddition and subsequent fragmentation. The structures of 11d and 12 were established by X-ray crystallography.

Abstract

The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-
2H-imidazol-2-ylidene)malononitriles 11, respectively, depending on the solvent used. In one example, a 1 : 1 complex, 12, of the 1H-imidazole 3-oxide and hexafluoroacetone hydrate was isolated as a second product. The formation of the products is explained by a stepwise 1,3-dipolar cycloaddition and subsequent fragmentation. The structures of 11d and 12 were established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2006
Deposited On:06 Dec 2011 08:01
Last Modified:26 Jan 2017 08:50
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Polish State Committee for Scientific Research (grant No. PBZ-KBN-126/T09/12), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200690129

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