The Effect of Ring-Size on the Anodic Oxidation of 'Cyclic Amides' in Methanol

Tatiana Golub, James Y. Becker

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The anodic oxidation of three 'cyclic amides' of type N-acylazacycloalkanes [5- (I), 6- (II) and 7-membered (III) rings] has been studied in methanol under constant current electrolysis, at C anodes and in the presence of various supporting electrolytes, and different concentrations of substrates. Four major products were formed in good yields by all three substrates, namely N-acyl, α-azacycloalkenes, N-acyl, α-methoxyazacycloalkanes, N-acyl, α-methoxy, α'-azacycloalkenes and N-acyl, α,α′-dimethoxyazacycloalkanes. The relative ratios among products and selectivity were found to be highly dependent on the nature of the electrolyte used, and to a lesser extent on substrate concentration. In terms of ring-size effect it was found that the rate of oxidation and current efficiency (yield) was in the order: I > II > III. Also the latter two behaved similarly (but different from I) when various supporting electrolytes were used.

Original languageEnglish
Pages (from-to)207-214
Number of pages8
JournalElectrochimica Acta
Volume205
DOIs
StatePublished - 1 Jul 2016

Keywords

  • N-acyl α α′-dimethoxyazacycloalkanes
  • N-acyl α-azacycloalkenes
  • N-acyl α-methoxy α′-azacycloalkenes
  • N-acyl α-methoxyazacycloalkanes

Fingerprint

Dive into the research topics of 'The Effect of Ring-Size on the Anodic Oxidation of 'Cyclic Amides' in Methanol'. Together they form a unique fingerprint.

Cite this