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

Justin Bours; Martha Morton; Albert J. Fry

doi:10.1016/j.tetlet.2011.12.072

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

Justin Bours, Martha Morton, Albert J. Fry

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

12 Scopus citations

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 language	English (US)
Pages (from-to)	1015-1017
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.072
State	Published - Feb 29 2012
Externally published	Yes

Keywords

Anodic oxidation
Carbocationic cyclization
Cyclooctatetraene
Homotropylium ion
β-silyl cation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.12.072

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title = "Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization",

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.",

keywords = "Anodic oxidation, Carbocationic cyclization, Cyclooctatetraene, Homotropylium ion, β-silyl cation",

author = "Justin Bours and Martha Morton and Fry, {Albert J.}",

note = "Funding Information: Financial support for this research was provided by Wesleyan University. Exact mass measurements were carried out by the Mass Spectrometry Facility at the University of California at Riverside, supported financially by NSF grant CHE-0742001. We would like to thank the NIH-NCRR-SIG program for funding the Varian Inova 600 spectrometer at the University of Connecticut in 2003. ",

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T1 - Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization

AU - Bours, Justin

AU - Morton, Martha

AU - Fry, Albert J.

N1 - Funding Information: Financial support for this research was provided by Wesleyan University. Exact mass measurements were carried out by the Mass Spectrometry Facility at the University of California at Riverside, supported financially by NSF grant CHE-0742001. We would like to thank the NIH-NCRR-SIG program for funding the Varian Inova 600 spectrometer at the University of Connecticut in 2003.

PY - 2012/2/29

Y1 - 2012/2/29

N2 - 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.

AB - 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.

KW - Anodic oxidation

KW - Carbocationic cyclization

KW - Cyclooctatetraene

KW - Homotropylium ion

KW - β-silyl cation

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

Abstract

Keywords

ASJC Scopus subject areas

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