- Electrochemical fluorination of aliphatic secondary amines
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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).
- Abe, Takashi,Hayashi, Eiji,Baba, Hajime
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- The synthesis of perfluoroamine using nitrogen trifluoride
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The reactions of nitrogen trifluoride (1) with hexafluoropropene (2) in the presence of cesium fluoride (CsF) gave 2- (3) and 1-heptafluoropropyldifluoroamine (4) in moderate yields. Tetrafluoroethylene (6) and octafluoro-2-butene (8) similarly reacted with 1 to give corresponding products.
- Takagi, Toshiyuki,Tamura, Masanori,Shibakami, Motonari,Quan, Heng-Dao,Sekiya, Akira
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