The effect of N-acyl and N-sulfonyl groups on the anodic methoxylation of piperidine derivatives

Tatiana Golub, James Y. Becker

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

N-acyl (-CHO, -COMe, -COOMe, -COPh, -COCF3) and N-sulfonyl (-SO2Me, -SO2Ph, -SO2 (p-tolyl) piperidines were synthesized and studied by cyclic voltammetry. Their anodic methoxylation was performed at various anodes (carbon rod, carbon felt, glassy carbon, Pt and PbO2), in the presence of different electrolytes (But4NClO4, Et4NBF4 and Et4NOTs), applying a current density of 20 mA cm-2. Methoxylation on graphite with Et4NOTs favored the formation of α-monomethoxy products whereas in the presence of Et4NBF4, the α,α'-dimethoxy derivatives become predominant in selected cases.

Original languageEnglish
Pages (from-to)408-415
Number of pages8
JournalElectrochimica Acta
Volume173
DOIs
StatePublished - 10 Aug 2015

Keywords

  • Anodic methoxylation
  • Constant current electrolysis
  • Cyclic voltammetry
  • N-acylpiperidines
  • N-sulfonylpiperidines

ASJC Scopus subject areas

  • Chemical Engineering (all)
  • Electrochemistry

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