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 | |
| State | Published - Feb 29 2012 |
Fingerprint
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 journal › Article
}
TY - JOUR
T1 - Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization
AU - Bours, Justin
AU - Morton, Martha D
AU - Fry, Albert J.
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
UR - http://www.scopus.com/inward/record.url?scp=84856232808&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84856232808&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2011.12.072
DO - 10.1016/j.tetlet.2011.12.072
M3 - Article
VL - 53
SP - 1015
EP - 1017
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 9
ER -