Abstract
Oxatriquinane, a fused, tricyclic alkyl oxonium ion of unprecented stability, was synthesized in five steps from 1,4,7-cyclononatriene. It survives reflux in H2O, chromatography, and attack by alcohols, alkyl thiols, halide ions, and hindered amine bases. The X-ray crystal structure shows longer C-O bond distances and more acute C-O-C bond angles than any reported alkyloxonium salt. The corresponding oxatriquinene and oxatriquinacene were also synthesized and represent the first examples of stable allyl oxonium species.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 13532-13533 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 130 |
| Issue number | 41 |
| DOIs | |
| State | Published - Oct 15 2008 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Oxatriquinane and oxatriquinacene : Extraordinary oxonium ions. / Mascal, Mark; Hafezi, Nema; Meher, Nabin K.; Fettinger, James C.
In: Journal of the American Chemical Society, Vol. 130, No. 41, 15.10.2008, p. 13532-13533.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Oxatriquinane and oxatriquinacene
T2 - Extraordinary oxonium ions
AU - Mascal, Mark
AU - Hafezi, Nema
AU - Meher, Nabin K.
AU - Fettinger, James C.
PY - 2008/10/15
Y1 - 2008/10/15
N2 - Oxatriquinane, a fused, tricyclic alkyl oxonium ion of unprecented stability, was synthesized in five steps from 1,4,7-cyclononatriene. It survives reflux in H2O, chromatography, and attack by alcohols, alkyl thiols, halide ions, and hindered amine bases. The X-ray crystal structure shows longer C-O bond distances and more acute C-O-C bond angles than any reported alkyloxonium salt. The corresponding oxatriquinene and oxatriquinacene were also synthesized and represent the first examples of stable allyl oxonium species.
AB - Oxatriquinane, a fused, tricyclic alkyl oxonium ion of unprecented stability, was synthesized in five steps from 1,4,7-cyclononatriene. It survives reflux in H2O, chromatography, and attack by alcohols, alkyl thiols, halide ions, and hindered amine bases. The X-ray crystal structure shows longer C-O bond distances and more acute C-O-C bond angles than any reported alkyloxonium salt. The corresponding oxatriquinene and oxatriquinacene were also synthesized and represent the first examples of stable allyl oxonium species.
UR - http://www.scopus.com/inward/record.url?scp=53849145033&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=53849145033&partnerID=8YFLogxK
U2 - 10.1021/ja805686u
DO - 10.1021/ja805686u
M3 - Article
C2 - 18798616
AN - SCOPUS:53849145033
VL - 130
SP - 13532
EP - 13533
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 41
ER -