Synthesis and reactions of fluoroalkyl polynitrogen compounds

α-Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species

“…Numerous N -trifluoromethyl-bearing imines are known indeed, although no universal method for their synthesis exists. In general, their preparation relies on the use of highly reactive N-CF 3 species such as trifluoronitrosomethane, difluoromethylene- N -(trifluoromethyl)amine, bis(trifluoromethyl)methylene- N -(trifluoromethyl)amine, tetrafluoroethylidene- N -(trifluoromethyl)amine, hexafluoropropylidene- N -(trifluoromethyl)amine, 2,2-bis(trifluoromethyl)tetrafluoropropylidine- N -(trifluoromethyl)amine, and trifluoromethylisocyanide …”

“…120 A few naked fluoropyranes have also been reported. The most remarkable model compound outside the sugar family is that of the 2,2,4,4-tetrafluoro-1,8,8trimethyl-3-oxybicyclo[3.2.1]octane (67). 121 Unfortunately, no crystal structure is yet available.…”

Mechanistic Study on the Fluorination of K[B(CN)4] with ClF Enabling the High Yield and Large Scale Synthesis of K[B(CF3)4] and K[(CF3)3BCN]

“…The [B(CF 3 ) 4 ] − anion is accessible by fluorination of the tetracyanoborate anion, [B(CN) 4 ] − , with either ClF or ClF 3 . In contrast, related reactions of nitriles with chlorine fluorides result in most cases in simple addition reactions to the R–CN triple bond yielding R–CF 2 –NCl 2 or R–CF 2 –NFCl compounds. − So far, the formation of CH 3 –CF 3 as a side product and in 45% yield has only been observed for the fluorination of acetonitrile with ClF 5 and ClF/F 2 , respectively. There is only one further example known in which the fluorination with ClF results in the partial cleavage of CF 2 –NCl 2 bonds .…”