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Triquinane is more often used in the natural product literature to refer to three angularly fused cyclopentane rings sharing a common quaternary carbon in the center, a structure which contains one more carbon atom at the periphery. Moreover, substitution by O is more properly designated by the
456:
prefix oxonia. Nevertheless, the authors who first prepared the cation called it oxatriquinane, and the name has been perpetuated in the literature. A semisystematic name in line with standard nomenclature would be 2a-oxonia-1,2,3,4,5,6-hexahydrotriquinacene.
415:-butyloxatriquinane has also been synthesized. This compound contains significant amounts of intramolecular steric strain, resulting in further bond elongation to give C–O bond lengths of 1.622 Å, the longest recorded in any species.
624:
Gunbas, Gorkem; Hafezi, Nema; Sheppard, William L.; Olmstead, Marilyn M.; Stoyanova, Irini V.; Tham, Fook S.; Meyer, Matthew P.; Mascal, Mark (18 November 2012). "Extreme oxatriquinanes and a record C–O bond length".
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and are hydrolytically sensitive. Oxatriquinane does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger
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such as hydroxide, cyanide, and azide. The ability of the oxygen to enter into a fourth covalent bond has been of some theoretical interest and was achieved using
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575:
Stoyanov, Evgenii S.; Gunbas, Gorkem; Hafezi, Nema; Mascal, Mark; Stoyanova, Irini V.; Tham, Fook S.; Reed, Christopher A. (11 January 2012).
480:
Mark Mascal; Nema Hafezi; Nabin K. Meher & James C. Fettinger (2008). "Oxatriquinane and
Oxatriquinacene: Extraordinary Oxonium Ions".
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1, 4, and 7, forming three fused pentagonal rings. In contrast to most trialkyloxonium ions, oxatriquinane hydrolyzes slowly.
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678:
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411:, which is of interest as a possible precursor to oxaacepentalene, a neutral aromatic species. 1,4,7-Tri-
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421:
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517:"Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents"
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395:, oxygen compounds routinely have bonds to >3 elements in other classes of compounds.
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Oxatriquinane was first described in 2008. Its five-step synthesis starts from
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577:"The R3O···H Hydrogen Bond: Toward a Tetracoordinate Oxadionium(2+) Ion"
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371:. Its C–O bond lengths are 1.54 Å. The C−O−C angles are acute.
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InChI=1S/C9H15O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h7-9H,1-6H2/q+1/t7-,8+,9-
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Except where otherwise noted, data are given for materials in their
204:
InChI=1/C9H15O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h7-9H,1-6H2/q+1/t7-,8+,9-
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391:. As illustrated by the structures of most
75:)-Octahydro-2aλ-oxacyclopentapentalene-2a(1
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581:Journal of the American Chemical Society
482:Journal of the American Chemical Society
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515:Rachel Petkewich (September 29, 2008).
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197:Key: BVKXDOLLNZJDKZ-AYMMMOKOSA-N
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207:Key: BVKXDOLLNZJDKZ-AYMMMOKOBR
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14:
548:"Oxonium ions: Ring of stability"
379:Oxonium ions normally are strong
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351:backbone, with a tricoordinated
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286:(at 25 °C , 100 kPa).
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1:
521:Chemical and Engineering News
546:Tim Reid (3 October 2008).
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329:oxoniaperhydrotriquinacene
533:10.1021/cen-v086n039.p010
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403:Related species include
407:, the tri-unsaturated
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369:1,4,7-cyclononatriene
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59:Preferred IUPAC name
679:Oxygen heterocycles
639:2012NatCh...4.1018G
488:(41): 13532–13533.
276: g·mol
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647:10.1038/nchem.1502
313:Infobox references
228:123(CC2)()CC3()CC1
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35:
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674:Oxonium compounds
633:(12): 1018–1023.
593:10.1021/ja209942s
494:10.1021/ja805686u
381:alkylating agents
321:Chemical compound
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127:Interactive image
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552:Nature Chemistry
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335:with formula (CH
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439:Oxaacepentalene
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427:Oxatriquinacene
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405:oxatriquinacene
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587:(1): 707–714.
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389:carborane acid
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20:Oxatriquinane
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355:connected to
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347:O. It has a
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393:metal oxides
385:nucleophiles
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103:1056549-35-9
86:Identifiers
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349:cyclononane
333:oxonium ion
237:Properties
668:Categories
527:(39): 10.
461:References
269:Molar mass
138:ChemSpider
114:3D model (
93:CAS Number
375:Reactions
655:23174982
611:22133059
502:18798616
172:57459997
147:21402960
635:Bibcode
602:3257418
399:Analogs
363:History
306:what is
304: (
274:139.218
159:PubChem
79:)-ylium
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409:analog
357:carbon
353:oxygen
301:verify
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221:SMILES
53:Names
445:Notes
186:InChI
116:JSmol
651:PMID
607:PMID
498:PMID
413:tert
643:doi
597:PMC
589:doi
585:134
556:doi
529:doi
490:doi
486:130
343:CH)
162:CID
71:,6a
67:,4a
63:(2a
16:Ion
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468:^
450:1.
339:CH
259:15
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631:4
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345:3
341:2
337:2
327:(
296:N
262:O
256:H
253:9
250:C
118:)
77:H
73:s
69:s
65:s
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