NIPPON KAGAKU KAISHI
Print ISSN : 0369-4577
Electrolytic Benzoyloxylation of N, N-Disubstituted Formamides, N-Substituted Lactams, and N-Substituted Cyclic lmides
Sriji ArataNobuko HiraiYukio NishimuraKenjiro Takeshita
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Volume 1973 (1973) Issue 11 Pages 2160-2165

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Abstract

The electrolytic benzoxylation of N, N-disubstituted formamides, N-methyllactams, and cyclic N-methyl imides with benzoic acid has been studiedi with N, N-disubstituted formamides, the current efficiency for the formation of ester-amides decreased as bulkiness of the substituent increased. The steric effect of N-alkyl groups was conspicuous. ln the case of N-methylformanilide, electrolytic benzoxylation did not occur, and this fact might be due probably to the presence of ev-phenyl group to nitrogen atom. Electrolysis of formamides of eyclic amine and N-methyllactams at low current density gave ester-amides in high current effciency. In the electrolytic benzoxylatien of N-methylsuccinimide the correponding ester-amide was produced in very low yield, and the reaction did not occur at all in the case of N-methylphthalimide. Ester-amides had a benzoylexy group substituted at α -position to nitrogen atom. ln the case of N-methyllactams and cyclic N-methyl imides substitution occurred at N-methyl group. This fact shows that the benzoyloxy group does not attack the methylene group in a ring.

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