382-28-5Relevant articles and documents
ELECTROCHEMICAL PRODUCTION OF PARTIALLY FLUORINATED ORGANIC COMPOUNDS: N-METHYLMORPHOLINE FLUORINATION
Gambaretto, G. P.,Napoli, M.,Fraccaro, C.,Conte, L.
, p. 427 - 436 (1982)
The usual electrochemical fluorination of organic compounds in anhydrous HF produces completely fluorinated materials.In order to obtain partially fluorinated compounds, electrofluorination has been conducted under various conditions, including the use of solvents.None of the solvents lead to satisfactory results.Experiments have also been carried out with high concentrations of N-methylmorpholine in anhydrous HF and they have provided information about the selectivity and the mechanism of the reaction.Various partially fluorinated derivatives of N-methylmorpholine have been identified, and some of them separated from the reaction mixture.
Electrochemical fluorination: State of the art and future tendences
Conte, Lino,Gambaretto, Gian Paolo
, p. 139 - 144 (2004)
A brief survey of the ECF process for the preparation of perfluorinated organo-compounds is given. The yield of perfluorinated products depends on the experimental conditions and on the nature of the starting material. Some useful rules are reported in order to optimise the ECF process. An improved operational technique allowed to obtain high yield of perfluorodimorpholinepropane (PFDMP) by simultaneous fluorination of dimorpholinepropane and N -methylmorpholine.
Electrochemical fluorination of (N,N-dialkylamino)alcohols
Abe, Takashi,Fukaya, Haruhiko,Hayashi, Eiji,Ono, Taizo,Nishida, Masakazu,Soloshonok, Irina,Okuhara, Kunio
, p. 229 - 237 (2007/10/03)
Series of amino alcohols including 2-(N,N-dialkylamino)ethanols, 3-(N,N-dimethylamino)propanol and 4-(N,N-dimethylamino)butanol were subjected to electrochemical fluorination. In the case of 2-(N,N-dialkylamino)ethanols, the F-(2-N,N-dialkylamino)acetyl fluorides were obtained in fair to good yields. Yields of each target compound were strongly dependent on the kind of the dialkylamino group. Cyclic amines having an N-(2-hydroxylethyl) group afforded the corresponding F-[N-(c-alkylamino)-substituted acetyl fluorides]. Their yields were generally better than those of acyclic analogs. Several 2-(N,N-dialkylamino)ethanols and 3-(N,N-dimethylamino)propanol were converted into the corresponding trimethylsilylethers, aminoalkyl methyl carbonates and bis-aminoalkyl carbonate, respectively, and they were subjected to fluorination for a comparison of the yield with that obtained from that of the parent aminoalcohol.
The electrochemical fluorination of N-containing carboxylic acids (Part 4). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-dialkylamino-n-butyrates
Abe, Takashi,Fukaya, Haruhiko,Hayashi, Eiji,Hayakawa, Yoshio,Nishida, Masakazu,Baba, Hajime
, p. 193 - 202 (2007/10/02)
Several methyl esters of 3-dialkylamino-substituted n- and isobutyric acids have been subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides.Dimethyl, diethyl, pyrrolidino, morpholino, piperidino and N-methylpiperazino groups were investigated as dialkylamino substituents.The structure/yield relationship was evaluated both in terms of the structure of the acid and the kind of amino group, respectively.Better yields of perfluoroacid fluorides were obtained from methyl esters having isobutyric acid skeletons than those having n-butyric acid groups, and from the acids containing cyclic amino groups than those containing acyclic ones.