815-29-2Relevant 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).
