Oxatriquinacene

Oxatriquinacene

Names
IUPAC name (2as,4as,6as)-4a,6a-Dihydro-2aH-6b-oxoniacyclopenta[cd]pentalene
Identifiers
ChemSpider	32675183
Jmol interactive 3D	Image
InChI InChI=1S/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9- Key: YQBOZXASCNTXGC-AYMMMOKOSA-N InChI=1/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9- Key: YQBOZXASCNTXGC-AYMMMOKOBA
SMILES C1=C[C@@H]2[O+]3[C@H]1C=C[C@@H]3C=C2
Properties
Chemical formula	C9H9O
Molar mass	133.167
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Oxatriquinacene is an organic cation with formula C
12H
9O+
. It is an oxonium ion, with a trivalent oxygen atom with +1 charge connected to carbons 1,4, and 7 of a cyclononatriene ring, forming three fused pentagonal cycles. The compound may possess weak tris-homoaromatic character.

Oxatriquinacene has remarkable stability compared to other oxonium cations, although not as extreme as that of the similar oxatriquinane. It reacts with water, but can be dissolved in acetonitrile. It is of interest as a possible precursor to oxaacepentalene, a hypothetical neutral aromatic species.^[1]

Oxatriquinacene was obtained in 2008 by Mascal and others, through a variant of the synthesis that led them to oxatriquinane.^[1][2][3]

See also

• Triethyloxonium tetrafluoroborate
• Brookhart's acid
• Pyrylium salt

References

1. Mark Mascal, Nema Hafezi, Nabin K. Meher, and James C. Fettinger (2008). "Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions". Journal of the American Chemical Society 130 (41): 13532–13533. doi:10.1021/ja805686u. PMID 18798616.
2. Rachel Petkewich (September 29, 2008). "Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents". Chemical and Engineering News 86 (39): 10. doi:10.1021/cen-v086n039.p010.
3. Tim Reid (3 October 2008). "Oxonium ions: Ring of stability". Nature Chemistry. doi:10.1038/nchem.70.