Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization

Justin Bours, Martha D Morton, Albert J. Fry

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Anodic oxidation of cyclooctatetraene (COT) was carried out in acetonitrile containing excess allyltrimethylsilane. Under these conditions COT is oxidized preferentially to afford the COT cation radical, which then undergoes nucleophilic attack by the silane followed by further anodic oxidation. The process results in a substance in which the original eight carbons of COT are highly differentiated by the addition of three allyl groups and the formation of two new rings.

Original languageEnglish (US)
Pages (from-to)1015-1017
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number9
DOIs
StatePublished - Feb 29 2012

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Silanes
Electrochemical oxidation
Anodic oxidation
Cations
Carbon
allyltrimethylsilane
acetonitrile

Keywords

  • Anodic oxidation
  • Carbocationic cyclization
  • Cyclooctatetraene
  • Homotropylium ion
  • β-silyl cation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization. / Bours, Justin; Morton, Martha D; Fry, Albert J.

In: Tetrahedron Letters, Vol. 53, No. 9, 29.02.2012, p. 1015-1017.

Research output: Contribution to journalArticle

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