Extraordinary Modes of Bonding Enabled by the Triquinane Framework

Gunbas G., MASCAL M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.78, sa.19, ss.9579-9583, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 78 Sayı: 19
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1021/jo401715s
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.9579-9583
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.