Extraordinary Modes of Bonding Enabled by the Triquinane Framework

Date

2013-10-04

Author

Günbaş, Emrullah Görkem

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Incorporation of triquinane ring systems into a macrobicyclic framework enables the stabilization of unusual bonding arrangements, including 3-center-2-electron cation, 3-center-3-electron radical, and 3-center-4-electron anion systems, linear divalent fluorine, triplet carbenes, record short C-C bonds, a powerful proton sponge effect, and oxadionium (R4O2+) ions. The means to stabilize and conceivably isolate such species derives from the rigid, convex nature of the triquinane ring system, as well as the substitution of positions adjacent to the bridgeheads atoms which would otherwise be vulnerable to elimination. The potential realization of hitherto undescribed bonding outcomes makes these macrocycles provocative synthetic targets.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/46522

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo401715s

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Department of Chemistry, Article

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Citation Formats

E. G. Günbaş, “Extraordinary Modes of Bonding Enabled by the Triquinane Framework,” JOURNAL OF ORGANIC CHEMISTRY, pp. 9579–9583, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/46522.