Anodic oxidation of α-silylacetic acids: Effects of anode material, current density and concentration on competing decarboxylation and desilylation processes

Libi Brakha; James Y. Becker

doi:10.1016/j.electacta.2012.05.089

Anodic oxidation of α-silylacetic acids: Effects of anode material, current density and concentration on competing decarboxylation and desilylation processes

Libi Brakha
, James Y. Becker

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

A model acid, Ph ₂(Me)SiCH ₂COOH, undergoes two competing anodic reactions, decarboxylation and desilylation under non-Kolbe conditions (e.g., at a C anode, in MeOH). The effects of anode material, current density, substrate concentration and base concentration on the two competing reactions have been investigated. The scope of the reaction was extended to other α-silyacetic acids of type R ₂R′SiCH ₂COOH, in order to study the influence by the substituents attached to silicon on the nature and distribution of products emerged from electrolysis.

Original language	English
Pages (from-to)	143-149
Number of pages	7
Journal	Electrochimica Acta
Volume	77
DOIs	https://doi.org/10.1016/j.electacta.2012.05.089
State	Published - 30 Aug 2012

Keywords

Anodic decarboxylation
Anodic desilylation
Kolbe electrolysis
α-Silylacetic acids

ASJC Scopus subject areas

General Chemical Engineering
Electrochemistry

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10.1016/j.electacta.2012.05.089

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@article{38f1cc661da7462f99f5fe542d56c159,

title = "Anodic oxidation of α-silylacetic acids: Effects of anode material, current density and concentration on competing decarboxylation and desilylation processes",

abstract = "A model acid, Ph 2(Me)SiCH 2COOH, undergoes two competing anodic reactions, decarboxylation and desilylation under non-Kolbe conditions (e.g., at a C anode, in MeOH). The effects of anode material, current density, substrate concentration and base concentration on the two competing reactions have been investigated. The scope of the reaction was extended to other α-silyacetic acids of type R 2R′SiCH 2COOH, in order to study the influence by the substituents attached to silicon on the nature and distribution of products emerged from electrolysis.",

keywords = "Anodic decarboxylation, Anodic desilylation, Kolbe electrolysis, α-Silylacetic acids",

author = "Libi Brakha and Becker, \{James Y.\}",

note = "Funding Information: This work was supported (in part) by the Israel Science Foundation (grant no. 762/11 ). The authors are thankful to Mrs. E. Solomon for technical assistance. JYB is thankful to Mrs. Irene Evens for supporting this research. ",

year = "2012",

month = aug,

day = "30",

doi = "10.1016/j.electacta.2012.05.089",

language = "English",

volume = "77",

pages = "143--149",

journal = "Electrochimica Acta",

issn = "0013-4686",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Anodic oxidation of α-silylacetic acids

T2 - Effects of anode material, current density and concentration on competing decarboxylation and desilylation processes

AU - Brakha, Libi

AU - Becker, James Y.

N1 - Funding Information: This work was supported (in part) by the Israel Science Foundation (grant no. 762/11 ). The authors are thankful to Mrs. E. Solomon for technical assistance. JYB is thankful to Mrs. Irene Evens for supporting this research.

PY - 2012/8/30

Y1 - 2012/8/30

N2 - A model acid, Ph 2(Me)SiCH 2COOH, undergoes two competing anodic reactions, decarboxylation and desilylation under non-Kolbe conditions (e.g., at a C anode, in MeOH). The effects of anode material, current density, substrate concentration and base concentration on the two competing reactions have been investigated. The scope of the reaction was extended to other α-silyacetic acids of type R 2R′SiCH 2COOH, in order to study the influence by the substituents attached to silicon on the nature and distribution of products emerged from electrolysis.

AB - A model acid, Ph 2(Me)SiCH 2COOH, undergoes two competing anodic reactions, decarboxylation and desilylation under non-Kolbe conditions (e.g., at a C anode, in MeOH). The effects of anode material, current density, substrate concentration and base concentration on the two competing reactions have been investigated. The scope of the reaction was extended to other α-silyacetic acids of type R 2R′SiCH 2COOH, in order to study the influence by the substituents attached to silicon on the nature and distribution of products emerged from electrolysis.

KW - Anodic decarboxylation

KW - Anodic desilylation

KW - Kolbe electrolysis

KW - α-Silylacetic acids

UR - https://www.scopus.com/pages/publications/84863728814

U2 - 10.1016/j.electacta.2012.05.089

DO - 10.1016/j.electacta.2012.05.089

M3 - Article

AN - SCOPUS:84863728814

SN - 0013-4686

VL - 77

SP - 143

EP - 149

JO - Electrochimica Acta

JF - Electrochimica Acta

ER -

Anodic oxidation of α-silylacetic acids: Effects of anode material, current density and concentration on competing decarboxylation and desilylation processes

Abstract

Keywords

ASJC Scopus subject areas

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