Oxatriquinane | |
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(2as,4as,6as)-Octahydro-1H-2a1-oxacyclopenta[cd]pentalen-2a1-ium |
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Identifiers | |
CAS number | 1056549-35-9 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C9H15O |
Molar mass | 139.21 g mol−1 |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Oxatriquinane is an alkyl oxonium ion with formula C9H15O+, remarkable for being stable in aqueous solution. It has a cyclononane backbone, with the trivalent oxygen connected to carbons 1,4, and 7, forming three fused pentagonal cycles.
Oxonium ions normally are strong alkylating agents and are only observed in solution as reactive intermediates or under extreme conditions. Oxatriquinane does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger nucleophiles such as hydroxide, cyanide, and azide. Oxatriquinane was first described in 2008, and was obtained after a five-step synthesis starting from cyclononatriene.[1][2][3] The same paper also described oxatriquinacene, the tri-unsaturated analog, which is of interest as a possible precursor to oxaacepentalene, a neutral aromatic species.