A new method for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids

Alex V. Shtelman; James Y. Becker

doi:10.1016/j.electacta.2009.06.050

A new method for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids

Alex V. Shtelman, James Y. Becker

Department of Chemistry

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

11 Scopus citations

Abstract

A new method has been developed for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids. Preparative electrolysis was carried out by constant current technique. The effect of various parameters (electricity consumption, current density, temperature, solvent, base and concentration of substrate) on the outcome of electrolytic process has been studied and evaluated. On the basis of optimal conditions found, the synthesis of three dimeric products Ph₂(Me)SiCH₂CH₂Si(Me)Ph₂, Ph(Me)₂SiCH₂CH₂Si(Me)₂Ph and Me₃SiCH₂CH₂SiMe₃ was achieved in good yields by anodic decarboxylation of the corresponding acids Ph₂(Me)SiCH₂CO₂H, Ph(Me)₂SiCH₂CO₂H and Me₃SiCH₂CO₂H.

Original language	English
Pages (from-to)	6696-6699
Number of pages	4
Journal	Electrochimica Acta
Volume	54
Issue number	26
DOIs	https://doi.org/10.1016/j.electacta.2009.06.050
State	Published - 1 Nov 2009

Keywords

Anodic oxidation
Disilylalkanes
Kolbe electrolysis
α-Silylcarboxylic acids

ASJC Scopus subject areas

General Chemical Engineering
Electrochemistry

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10.1016/j.electacta.2009.06.050

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title = "A new method for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids",

abstract = "A new method has been developed for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids. Preparative electrolysis was carried out by constant current technique. The effect of various parameters (electricity consumption, current density, temperature, solvent, base and concentration of substrate) on the outcome of electrolytic process has been studied and evaluated. On the basis of optimal conditions found, the synthesis of three dimeric products Ph2(Me)SiCH2CH2Si(Me)Ph2, Ph(Me)2SiCH2CH2Si(Me)2Ph and Me3SiCH2CH2SiMe3 was achieved in good yields by anodic decarboxylation of the corresponding acids Ph2(Me)SiCH2CO2H, Ph(Me)2SiCH2CO2H and Me3SiCH2CO2H.",

keywords = "Anodic oxidation, Disilylalkanes, Kolbe electrolysis, α-Silylcarboxylic acids",

author = "Shtelman, {Alex V.} and Becker, {James Y.}",

note = "Funding Information: This research was supported (in part) by the Israel Science Foundation (grant No. 317/07). The authors are thankful to E. Solomon for technical assistance.",

year = "2009",

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doi = "10.1016/j.electacta.2009.06.050",

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T1 - A new method for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids

AU - Shtelman, Alex V.

AU - Becker, James Y.

N1 - Funding Information: This research was supported (in part) by the Israel Science Foundation (grant No. 317/07). The authors are thankful to E. Solomon for technical assistance.

PY - 2009/11/1

Y1 - 2009/11/1

N2 - A new method has been developed for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids. Preparative electrolysis was carried out by constant current technique. The effect of various parameters (electricity consumption, current density, temperature, solvent, base and concentration of substrate) on the outcome of electrolytic process has been studied and evaluated. On the basis of optimal conditions found, the synthesis of three dimeric products Ph2(Me)SiCH2CH2Si(Me)Ph2, Ph(Me)2SiCH2CH2Si(Me)2Ph and Me3SiCH2CH2SiMe3 was achieved in good yields by anodic decarboxylation of the corresponding acids Ph2(Me)SiCH2CO2H, Ph(Me)2SiCH2CO2H and Me3SiCH2CO2H.

AB - A new method has been developed for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids. Preparative electrolysis was carried out by constant current technique. The effect of various parameters (electricity consumption, current density, temperature, solvent, base and concentration of substrate) on the outcome of electrolytic process has been studied and evaluated. On the basis of optimal conditions found, the synthesis of three dimeric products Ph2(Me)SiCH2CH2Si(Me)Ph2, Ph(Me)2SiCH2CH2Si(Me)2Ph and Me3SiCH2CH2SiMe3 was achieved in good yields by anodic decarboxylation of the corresponding acids Ph2(Me)SiCH2CO2H, Ph(Me)2SiCH2CO2H and Me3SiCH2CO2H.

KW - Anodic oxidation

KW - Disilylalkanes

KW - Kolbe electrolysis

KW - α-Silylcarboxylic acids

UR - http://www.scopus.com/inward/record.url?scp=69249154327&partnerID=8YFLogxK

U2 - 10.1016/j.electacta.2009.06.050

DO - 10.1016/j.electacta.2009.06.050

M3 - Article

AN - SCOPUS:69249154327

SN - 0013-4686

VL - 54

SP - 6696

EP - 6699

JO - Electrochimica Acta

JF - Electrochimica Acta

IS - 26

ER -

A new method for the synthesis of disilylalkanes by Kolbe anodic oxidation of α-silylcarboxylic acids

Abstract

Keywords

ASJC Scopus subject areas

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