Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-12637
Mloston, G; Gendek, T; Linden, A; Heimgartner, H (2008). Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate. Polish Journal of Chemistry, 82(8):1561-1569.
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The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic reagents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.
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|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Deposited On:||06 Feb 2009 12:58|
|Last Modified:||05 Jun 2014 13:09|
|Publisher:||Polskie Towarzystwo Chemiczne|
|Funders:||Polish Ministry for Science and Higher Education, F. Hoffmann-La Roche AG, Basel|
|Related URLs:||http://ichf.edu.pl/pjch/ (Publisher)|
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