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Reactions of 2‐Unsubstituted 1 H ‐Imidazole 3‐Oxides with 2,2‐Bis(trifluoromethyl)ethene‐1,1‐dicarbonitrile: A Stepwise 1,3‐Dipolar Cycloaddition
Author(s) -
Mlostoń Grzegorz,
Jasiński Marcin,
Linden Anthony,
Heimgartner Heinz
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690129
Subject(s) - chemistry , cycloaddition , imidazole , trifluoromethyl , medicinal chemistry , hexafluoroacetone , oxide , fragmentation (computing) , 1,3 dipolar cycloaddition , hydrate , photochemistry , stereochemistry , organic chemistry , catalysis , alkyl , computer science , operating system
The reaction of 1,4,5‐trisubstituted 1 H ‐imidazole‐3‐oxides 1 with 2,2‐bis(trifluoromethyl)ethene‐1,1‐dicarbonitrile ( 7 , BTF) yielded the corresponding 1,3‐dihydro‐2 H ‐imidazol‐2‐ones 10 and 2‐(1,3‐dihydro‐2 H ‐imidazol‐2‐ylidene)malononitriles 11 , respectively, depending on the solvent used. In one example, a 1 : 1 complex, 12 , of the 1 H ‐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.