Oxatriquinacene Explained

Oxatriquinacene is an organic cation with formula . It is an oxonium ion, with a tricoordinated 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.

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

See also

• Triethyloxonium tetrafluoroborate
• Brookhart's acid
• Pyrylium salt

Notes and References

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