Abstract
The electrolytic benzoyloxylation of N, N-dimethylamides, (CH2)2NCOR, with benzoic acid has been studied. At first, the electrolytic benzoyloxylation of N, N-dimethylformamide(DMF) with benzoic acid was investigated in benzene, dimethylsulfoxide(DMSO) and acetonitrile. The acetonitrile-DMF system using tetraethylammonium perchlorate as a supporting electrolyte gave the highest conversion at a low bath voltage. Therefore, acetonitrile was used as a solvent.
Electrolysis of benzoic acid in acetonitrile-(CH2)2NCOR gave selectively N-beRzoxymethyl-Nmethylcarboxamides(2), similarly to the electrolysis in DMF. Studies on the effect of R groups indicated that the current eMciency for the formation of (2) was not affeted by bulky groups such as isopropyl and cyclohexyl. The current efficiency for the'formation of (2) was remarkably decreased by the substitution of phenyl group. However, the introduction of methylene group between phenyl and carbonyl group showed the tendency of increasing current efficiency slightly.
