A. Takashi, H. Fukaya, T. Ono
Feb 2, 1998
Citations
0
Influential Citations
11
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Cis -2,6-dimethylmorpholine and its derivatives having an ester group were subjected to electrochemical fluorination. The electrochemical fluorination of cis -2,6-dimethylmorpholine afforded only a small quantity of F -( N -fluoro-2,6-dimethyl-morpholine), whereas the N -(methoxycarbonylalkyl)-substituted cis -2,6-dimethyl-morpholines gave the corresponding F -acid fluorides in fair yields. Cis -and trans -isomerization on two methyl substituents of the morpholine ring occurred through electrochemical fluorination of pure cis -2,6-dimethylmorpholine to give a 1:0.25–0.5 mixture of cis - and trans -isomers having a F -2,6-dimethylmorpholino-moiety. The formation of a seven-membered ring expanded product was confirmed as a by-product in the fluorination of methyl cis -2,6-dimethylmorpholino-acetate. Spectroscopic data as well as physical properties of new nitrogen-containing F -carboxylic acids are presented.