2344-11-8Relevant academic research and scientific papers
Electrochemical fluorination of aliphatic secondary amines
Abe, Takashi,Hayashi, Eiji,Baba, Hajime
, p. 35 - 42 (2007/10/03)
Electrochemical fluorination (ECF) has been examined for six aliphatic secondary amines: N,N-di-ethylamine, N-ethyl,N-n-propylamine, N,N-di-n-propylamine, N-ethyl,N-iso-propylamine, N,N-di-iso-propylamine, and N-methyl,N-n-butylamine. It was found from these amines that not only the corresponding F-(N-fluoro-N,N-dialkylamines) but also F-imines having the same number of the carbon atoms were formed in low yields. The suppression of the C-N bond cleavage (blocking effect) which is expected to occur during fluorination due to the presence of bulky N-alkyl group was not observed as a result of the ECF of these aliphatic secondary amines. It was also found that the change of the initial solute concentration of N,N-di-n-propylamine did not affect on the product yields, which is usually observed for cyclic secondary amines. Several F-(N-fluoro-N,N-dialkylamines) were treated with triphenylphosphine for conversion into the corresponding F-imines. An imine bond was generated during this defluorination exclusively at the site of the alkyl group with a longer chain length when there were two different alkyl groups present in F-(N-fluoro-dialkylamines).
Reactions and photochemistry of some fluorinated amines and imines
Peterman, Keith E.,Shreeve, Jean'ne M.
, p. 1223 - 1228 (2008/10/08)
Treatment of CF3C(O)N=C(CF3)2 (I) and CF3C(O)NClCF(CF3)2 (III) with PCl5 readily produces the imines CF3CCl2N=C(CF3)2 (II) and CF3CCl=NCF(CF3)2 (V), respectively. Catalytic chlorofluorination of II yields CF3CF2NClCF(CF3)2 (VIII) via a series of ClF addition and subsequent dechlorination steps. Polar addition of ClF to CF3CF2N=CFCF3 (XI) results in (CF3CF2)2NCl (XIII). The two chloramines VIII and XIII are converted to the perfluoroalkyl secondary amines CF3CF2NHCF(CF3)2 and (CF3CF2)2NH with HCl. Photolytic decomposition products of the chloramines, which include a new perfluoroalkyl asymmetric amine, CF3(CF3CF2)NCF(CF3)2 (XII), are identified. The mechanistic pathway for the photolytic decomposition of I is also presented. Copyright 1975 by the American Chemical Society.
