124008-11-3Relevant articles and documents
Electrochemical fluorination of 1-ethylpiperazine and 4-methyl- and/or 4-ethylpiperazinyl substituted carboxylic acid methyl esters
Abe, Takashi,Baba, Hajime,Soloshonok, Irina
, p. 21 - 35 (2007/10/03)
Electrochemical fluorination (ECF) of 1-ethylpiperazine and eight methyl esters of 4-methyl- and/or 4-ethylpiperazinyl substituted carboxylic acids were studied. Corresponding perfluoro(4-fluoro-1-ethylpiperazine) was obtained from 1-ethylpiperazine in a small yield along with perfluoro(1-methyl-3-ethylimidazolidine), perfluoro[2-(N′,N′-difluoroaminoethyl)-N,N-diethylamine)] and perfluorotriethylamine. The corresponding mono-basic perfluoroacid fluorides with a perfluoro(4-alkylpiperazinyl) group were obtained in fair to good yields from the fluorination of methyl esters of 4-alkylpiperazinyl-substituted carboxylic acids. Yields of the targeted perfluoro(4-alkylpiperazinyl) group containing perfluorocarboxylic acid fluorides varied depending on both the type of N-alkyl (alkyl=CH3- or C2H5-) group at the 4-position and the (ω-methoxycarbonylalkyl) group at the 1-position of the piperazine ring of the substrate. Higher yields of perfluoroacid fluorides were obtained by the ECF of 4-ethyl substituted piperazine derivatives than of the 4-methyl substituted piperazine derivatives when 4-alkylpiperazines with the same carboxylic acid ester group were fluorinated electrochemically. Spectroscopic data as well as physical properties are described for new perfluoro(1,4-dialkylpiperazines) and N-containing perfluorocarboxylic acids with a perfluoropiperazinyl group.
THE ELECTROCHEMICAL FLUORINATION OF NITROGEN-CONTAINING CARBOXYLIC ACIDS. FLUORINATION OF DIMETHYLAMINO- OR DIETHYLAMINO-SUBSTITUTED CARBOXYLIC ACID DERIVATIVES
Abe, Takashi,Hayashi, Eiji,Baba, Hajime,Fukaya, Haruhiko
, p. 257 - 279 (2007/10/02)
The electrochemical fluorination of six derivatives of dimethylamino- or diethylamino-substituted carboxylic acids has been conducted.As the main fluorination products, cyclized and cleaved products as well as the desired N-containing perfluoroacid fluorides were formed, and their ratios depended on the chain length and the structure of the starting carboxylic acids, and the nature of the dialkylamino group.Through this work, perfluoro(dimethylamino-acetyl fluoride), perfluoro(diethylamino-acetyl fluoride), perfluoro(2-dimethylamino-propionyl fluoride), perfluoro(2-dimethylamino-butyryl fluoride) and perfluoro(3-dimethylamino-propionyl fluoride) were prepared.Except for perfluoro(dimethylamino-acetyl fluoride), these acid fluorides were new compounds.The physical properties of new compounds obtained including these acid fluorides are reported together with their spectral (19F nmr, Mass and IR) data.
