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

Tatiana Golub; James Y. Becker

doi:10.1016/j.electacta.2015.04.133

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

Tatiana Golub, James Y. Becker

Department of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	408-415
Number of pages	8
Journal	Electrochimica Acta
Volume	173
DOIs	https://doi.org/10.1016/j.electacta.2015.04.133
State	Published - 10 Aug 2015

Keywords

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

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10.1016/j.electacta.2015.04.133

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title = "The effect of N-acyl and N-sulfonyl groups on the anodic methoxylation of piperidine derivatives",

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.",

keywords = "Anodic methoxylation, Constant current electrolysis, Cyclic voltammetry, N-acylpiperidines, N-sulfonylpiperidines",

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journal = "Electrochimica Acta",

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T1 - The effect of N-acyl and N-sulfonyl groups on the anodic methoxylation of piperidine derivatives

AU - Golub, Tatiana

AU - Becker, James Y.

PY - 2015/8/10

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N2 - 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.

AB - 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.

KW - Anodic methoxylation

KW - Constant current electrolysis

KW - Cyclic voltammetry

KW - N-acylpiperidines

KW - N-sulfonylpiperidines

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DO - 10.1016/j.electacta.2015.04.133

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VL - 173

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EP - 415

JO - Electrochimica Acta

JF - Electrochimica Acta

SN - 0013-4686

ER -

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

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