Trifluoroethyl group amines

The value of K has been measured for several amines with 2-methylpropanal. The effect of the structure of the alkyl group is quite small, although the trifluoroethyl group significantly reduces imine stability. 

The observation by Yarovenko and Raksha " in 1960 that diethyl (2-chloro-1,1,2-trifluoroethyl) amine (hereafter called fluoroamine ) could replace hydroxyl groups by fluorine was first applied in the steroid field byAyer and Knox and co-workers. These workers found that a methylene... 

Aromatic primary amines are not only binucleophiles at the amino group, but they also exhibit the properties of C,N-binucleophiles. Their reactions with internal perfluoroolefins lead to quinoline derivatives (98JFC(88)169, 94JCS(CC)134, 98T4949). Thus the reaction of aniline with 2//-heptafluorobut-2-ene yields phenyl(2-trifluoromethylquinolin-4-yl) amine (00ZOR109) when the reaction is carried out with the tetrafluoro-ethylene trimer, it leads to 2-trifluoromethyl-3-(l-N-phenylimino-2,2,2-trifluoroethyl)-4-(N-phenylamino)quinoline (98JFC(88)169). 

In contrast to the anodic methoxylation of A-(2,2,2-trifluoroethyl)amines, anodic cyanation does not occur at the position a to the trifluoroalkyl group (Scheme 48) [275]. 

The reaction leading to amine 3935 also affords some of the expected N-trifluoroethyl analog,12,43 and some reduction of the isoquinoline ring is observed with 40.36 The reduction of three benzophenone-type carbonyl groups in a tricalix[5]arene proceeded in 95% yield.44... 

Trifluoroethylidenation of activated CH2P The Polonovski reaction of dimethyl(trifluoroethyl)amine oxide with (CFjCOljO in the presence of a compound containing an active methylene group accomplishes trifluoroethylidenation at that site. 

Early accounts of non-metal catalysed transamidation used gaseous boron trifluoride with aeetamide and aniline vapor. However, recent boron-based reagents, although used in excess, work under eonsiderably milder conditions and tolerate a wide variety of functional groups. Sheppard and co-workers tris(trifluoroethyl)borate reagent, also highlighted for direct amide bond forming reactions between carbo>ylic acids and amines, is active for... 

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