29540-81-6Relevant articles and documents
TRIFLAZOLES AND METHODS OF MAKING THE SAME
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Paragraph 0102-0103, (2021/08/06)
Methods for producing triflazoles or related derivatives thereof, and the resulting products are provided. For example, triflazoles can be prepared by reaction of trifluoromethanesulfonyl fluoride with an azole or azolate salt. Yields up to 78% are obtained. Triflazoles can be prepared by the reaction of a trifluoromethanesulfonyl fluoride with an N-silylazole in the presence of a basic catalyst. Yields up to 97% are obtained.
Reaction of triflyl-imidazole with aldoximes: Facile synthesis of nitriles and formation of novel aldoxime-bis(N-triflyl)-imidazole adducts
Kalkhambkar, Rajesh G.,Bunge, Scott D.,Laali, Kenneth K.
supporting information; scheme or table, p. 5184 - 5187 (2011/10/13)
The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1:1 aldoxime-bis(N-triflyl)imidazole covalent adducts, in which the aldoxime oxygen atom is bonded to the imidazole C-2 ring carbon. For these aldoximes, conversion to nitrile could be effected by reaction with Tf2O in the absence of imidazole. The molecular structure of the adduct formed from 2-methyl-5-fluoro-benzaldoxime was confirmed by X-ray analysis. Plausible mechanisms for the formation of 1:1 covalent adducts have been considered. Various attempts to isolate such adducts via the reaction of an authentic sample of bis(N-triflyl)imidazolium trifate with aldoxime were unsuccessful. Remarkably, whereas isolated benzaldoxime adducts undergo deprotonation/methylation with NaH/MeI, an authentic sample of bis(N-triflyl)imidazolium triflate did not undergo H/Me exchange under these conditions. These transformations are discussed.
