564-11-4Relevant articles and documents
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.
THE ELECTROCHEMICAL FLUORINATION OF NITROGEN-CONTAINING CARBOXYLIC ACIDS. FLUORINATION OF METHYL ESTERS OF CYCLIC AMINOGROUP SUBSTITUTED CARBOXYLIC ACIDS
Abe, Takashi,Hayashi, Eiji,Fukaya, Haruhiko,Baba, Hajime
, p. 173 - 196 (2007/10/02)
Nine methyl esters of cyclic amino-group substituted carboxylic acids related to glycine, alanine or β-alanine were subjected to electrochemical fluorination.This afforded the corresponding perfluoroacid fluorides together with cleavage products in fair yields.As cyclic amino-substituents, pyrrolidino-, morpholino-, piperidino-, hexamethyleneimino- and N'-methylpiperazinyl-groups were investigated.The formation of cyclized by-products was not observed, which contrasts with the fluorination of aliphatic dialkylamino-substituted carboxylic acids.From such methyl 2-cyclic amino-propionates (cyclic amino-group: a pyrrolidino, a morpholino or a piperidino-group), the perfluorinated methyl esters were obtained together with the corresponding perfluoroacid fluorides in yields of 1-2percent and 14-29percent, respectively.The formation of the former compounds is ascribed to the blocking effect of the bulky cyclic amino-groups.The physical properties of the new compounds obtained are reported together with their spectral (19F NMR, Mass and IR) data.