Anodic oxidation of α-silylacetic acid Ph 2(Me)SiCH 2COOH: Decarboxylation versus desilylation

Libi Brakha, James Y. Becker

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Constant current electrolysis of Ph 2(Me)SiCH 2COOH in methanol under non-Kolbe conditions (carbon anode, low current density) undergoes two competing reactions: decarboxylation and desilylation. The oxidative-decarboxylation process involves both 1e - and 2e - and affords a Kolbe 'dimer' [Ph 2(Me)SiCH 2CH 2Si(Me)Ph 2] and non-Kolbe products of type Ph 2(Me)SiCH 2OCH 3 and Ph 2(Me) SiCH 2OH, respectively, whereas the 1e - desilylation process gives silylated products of type Ph 2(Me)SiOH, Ph 2(Me)SiOCH 3, Ph(Me)Si(OCH 3) 2 and the siloxane Ph 2(Me)SiOSi(Me)Ph 2. The effects of the polarity of the media and temperature on these two pathways have been investigated.

Original languageEnglish
Pages (from-to)135-139
Number of pages5
JournalElectrochimica Acta
Volume59
DOIs
StatePublished - 1 Jan 2012

Keywords

  • Anodic decarboxylation
  • Anodic desilylation
  • Non-Kolbe products
  • α-Silylacetic acid

Fingerprint

Dive into the research topics of 'Anodic oxidation of α-silylacetic acid Ph <sub>2</sub>(Me)SiCH <sub>2</sub>COOH: Decarboxylation versus desilylation'. Together they form a unique fingerprint.

Cite this