Oxatriquinane
Encyclopedia
Oxatriquinane is an alkyl oxonium ion
with formula , 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 nucleophile
s such as hydroxide, cyanide, and azide. Oxatriquinane was first described in 2008, and was obtained after a five-step synthesis starting from cyclononatriene. The same paper also described oxatriquinacene, the tri-unsaturated analog, which is of interest as a possible precursor to oxaacepentalene, a neutral aromatic species.
Oxonium ion
The oxonium ion in chemistry is any oxygen cation with three bonds. The simplest oxonium ion is the hydronium ion H3O+. Another oxonium ion frequently encountered in organic chemistry is obtained by protonation or alkylation of a carbonyl group e.g...
with formula , remarkable for being stable in aqueous solution. It has a cyclononane
Cyclononane
Cyclononane is an alicyclic hydrocarbon consisting of a ring of nine carbon atoms. Its molecular formula is C9H18. Its empirical formula is CH2....
backbone, with the trivalent oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
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 nucleophile
Nucleophile
A nucleophile is a species that donates an electron-pair to an electrophile to form a chemical bond in a reaction. All molecules or ions with a free pair of electrons can act as nucleophiles. Because nucleophiles donate electrons, they are by definition Lewis bases.Nucleophilic describes the...
s such as hydroxide, cyanide, and azide. Oxatriquinane was first described in 2008, and was obtained after a five-step synthesis starting from cyclononatriene. The same paper also described oxatriquinacene, the tri-unsaturated analog, which is of interest as a possible precursor to oxaacepentalene, a neutral aromatic species.