Extraordinary modes of bonding enabled by the triquinane framework

Gorkem Gunbas, Mark Mascal

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


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 (R4O 2+) 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.

Original languageEnglish (US)
Pages (from-to)9579-9583
Number of pages5
JournalJournal of Organic Chemistry
Issue number19
StatePublished - Oct 4 2013

ASJC Scopus subject areas

  • Organic Chemistry


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