Acepentalene

Acepentalene
Names
	Preferred IUPAC name Cyclopenta[cd]pentalene
	Other names Acepentylene
Identifiers
CAS Number	187-68-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	21477342 ;
PubChem CID	13484333;
CompTox Dashboard (EPA)	DTXSID20541925 ;
	InChI InChI=1S/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H Key: CUIAUPQXSDOJAG-UHFFFAOYSA-N ; InChI=1/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H Key: CUIAUPQXSDOJAG-UHFFFAOYAJ;
	SMILES C2(C=C3)=C1C3=CC=C1C=C2; C1=CC2=CC=C3C2=C1C=C3;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

^ 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.
^ 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.
^ 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.

[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.

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