Acepentalene

Last updated
Acepentalene
Acepentalene.png
Acepentalene-3D-balls.png
Names
Preferred IUPAC name
Cyclopenta[cd]pentalene
Other names
Acepentylene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H Yes check.svgY
    Key: CUIAUPQXSDOJAG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H
    Key: CUIAUPQXSDOJAG-UHFFFAOYAJ
  • C2(C=C3)=C1C3=CC=C1C=C2
  • C1=CC2=CC=C3C2=C1C=C3
Properties
C10H6
Molar mass 126.158 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acepentalene is a tricyclic anti-aromatic compound. Its molecular formula is C10H6. It consists of three five-membered rings fused across three of the five carbon atoms. The central carbon atom in acepentalene is part of all three rings. There are formally five double bonds in acepentalene, so that the molecule formally contains four double bonds on the exterior, and one double bond from the central carbon to the exterior of the ring system.

The acepentalene dianion, which can be stabilized by two lithium atoms, is more stable. The radical anion is also known. [1]

The dianion was first synthesized by reacting triquinacene with n-butyllithium and potassium tert-amylate (also called potassium t-pentoxide) in hexane solution. [2] [3]

References

  1. Armin de Meijere; Fabian Gerson; Peter R. Schreiner; Pascal Merstetter; Franz-Manfred Schüngel (1999). "The radical anion of acepentalene". Chem. Commun. (21): 2189–2190. doi:10.1039/a906972k.
  2. Lendvai, Thomas; Friedl, Thomas; Butenschön, Holger; Clark, Timothy; Meijere, Armin de (1986). "Dihydroacepentalenediide, the Dianion of Acepentalene" . Angewandte Chemie International Edition in English. 25 (8): 719–720. doi:10.1002/anie.198607191. ISSN   1521-3773.
  3. Haag, Rainer; Kuck, Dietmar; Fu, Xiao-Yong; Cook, James W.; DeMeijere, Armin (1994). "Facile Formation of Dihydroacepentalenediide from centro-Substituted Tribenzotriquinacenes with C-C Bond Cleavage" . Synlett. 1994 (5): 340–342. doi:10.1055/s-1994-22846. ISSN   0936-5214. S2CID   196822833.