2344-10-7Relevant articles and documents
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 nitrogen-containing carboxylic acids. Fluorination of methyl esters of 3-dialkylamino propionic acids
Abe, Takashi,Hayashi, Eiji,Fukaya, Haruhiko,Hayakawa, Yoshio,Baba, Hajime,et al.
, p. 101 - 111 (2007/10/02)
Six methyl esters of 3-dialkylamino-substituted propionic acids were subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides.The following dialkylamino substituents were investigated: diethylamino, di-n-propylamino, di-n-butylamino, pyrrolidino, morpholino and piperidino groups.These perfluoroacid fluorides, which were obtained in fair yields, are considered to be prospective key precursors for preparing soft-type (degradable) fluorochemicals.The salts show a considerable lowering of surface tension in aqueous solution.Thephysical properties of all the perfluoroacid fluorides obtained are reported, together with their spectroscopic data (19F NMR, mass and IR spectra).
FLUORINATIONS WITH COMPLEX METAL FLUORIDES. PART 7. FLUORINATIONS OF THE METHYL PYRIDINES WITH CAESIUM TETRAFLUOROCOBALTATE
Plevey, Raymond G.,Rendell, Richard W.,Tatlow, John Colin
, p. 265 - 286 (2007/10/02)
4-Methylpyridine passed over caesium tetrafluorocobaltate at 330-340 deg gave tridecafluoro(1,3-dimethylpyrrolidine) (1) and its 3-difluoromethyl analogue (2), together with a range of polyfluoro-4-picolines (4-10) with -CF3, -CHF2 or -CH2F groups in the 4-position. 3-Methylpyridine similarly gave 1 and its 1,2-isomer (11) together with several polyfluoro-3-picolines (14-18). 2-Methylpyridine at 270 deg gave tridecafluoro(1-ethylpyrrolidine) (13), a trace of 11 and 2-trifluoromethyl- (22), 2-difluoromethyl- (23) and 2-fluoromethyl-tetrafluoropyridine (24); there were also products arising by loss of methyl.Other unidentified fluoroalkylpyridines besides those isolated were present in each case.