𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Reactions of 2-Unsubstituted 1H-Imidazole 3-Oxides with 2,2-Bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A Stepwise 1,3-Dipolar Cycloaddition

✍ Scribed by Grzegorz Mlostoń; Marcin Jasiński; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
168 KB
Volume
89
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1dicarbonitrile (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.

1 ) Part of the planned Ph.D.

📜 SIMILAR VOLUMES

Reactions of Methyl Diazoacetate with (E
Reactions of Methyl Diazoacetate with (E)- and (Z)-1,2-Bis(trifluoromethyl)ethene-1,2-dicarbonitrile: Novel and Unanticipated Pathways
✍ Rolf Huisgen; Grzegorz Mlostoń; Peter Pöchlauer; Lubor Fišera; Henry Giera 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 190 KB

Dedicated to Mordecai Rubin, Technion, Haifa, on the occasion of his 80th birthday The cycloadditions of methyl diazoacetate to 2,3-bis(trifluoromethyl)fumaronitrile ((E)-BTE) and 2,3-bis(trifluoromethyl)maleonitrile ((Z)-BTE) furnish the 4,5-dihydro-1H-pyrazoles 13. The retention of dipolarophile

ChemInform Abstract: 1,3-Dipolar Cycload
ChemInform Abstract: 1,3-Dipolar Cycloaddition of Cyclic α-Methoxynitrones, Derivatives of 2H-Imidazole 1-Oxide and 4H-Imidazole 3-Oxide.
✍ S. M. Bakunova; I. A. Kirilyuk; I. A. Grigor'ev 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v