Basketene

Basketene
Names
	IUPAC name Pentacyclo[4.4.0.02,5.03,8.04,7]dec-9-ene
	Other names Bishomocubene
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	122156 ;
PubChem CID	138538;
CompTox Dashboard (EPA)	DTXSID30971411 ;
	InChI InChI=1S/C10H10/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h1-10H Key: LXQOIQYQFRKBLV-UHFFFAOYSA-N; InChI=1/C10H10/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h1-10H;
	SMILES C2=CC5C1C4C3C1C2C3C45;
Properties
Chemical formula	C10H10
Molar mass	130.186 g/mol
	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

Basketene (IUPAC name: pentacyclo[4.4.0.0^2,5.0^3,8.0^4,7]dec-9-ene^[1]) is an organic compound with the formula C₁₀H₁₀. It is a polycyclic alkene and the dehydrogenated version of basketane, which was named for its structural similarity to a basket.

Synthesis

Basketene has been synthesized by the isomerization of cyclooctatetraene followed by a Diels–Alder reaction with maleic anhydride. [2 + 2] cycloaddition closes the cage structure, which is converted to basketene by saponification and decarboxylation.^[2]

Reactions

Photolysis of basketene produces cyclooctatetraene, Nenitzescu's hydrocarbon and so on.^[3]

References

^ Verevkin, Sergei P.; Martin Kümmerlin; Ernst Hickl; Hans-Dieter Beckhaus; Christoph Rüchardt; Sergei I. Kozhushkov; Rainer Haag; Roland Boese; Jordi Benet-Bucholz; Karsten Nordhoff; Armin de Meijere (2002). "Thermochemical and X-ray Crystallographic Investigations of Some (CH)₁₀ Hydrocarbons: Basketene, Nenitzescu's Hydrocarbon, and Snoutene". European Journal of Organic Chemistry. 2002 (14). Wiley VCH: 2280–7. doi:10.1002/1099-0690(200207)2002:14<2280::AID-EJOC2280>3.0.CO;2-R. Archived from the original on 2013-01-05. Retrieved 2009-11-23.
^ Smit, William A.; Bochkov, Alekseĭ Feodosʹevich; Caple, Ron (1998). Organic synthesis: the science behind the art. Royal Society of Chemistry. p. 184. ISBN 978-0-85404-544-0. Retrieved 2008-12-10.
^ Allred, Evan L.; Beck, Boyd R. (1973). "Concurrent thermolysis and photolysis of basketene. Formation and the interrelation of some new (CH)₁₀ isomers". Journal of the American Chemical Society. 95 (7): 2393. doi:10.1021/ja00788a065.

[thermo-1] Verevkin, Sergei P.; Martin Kümmerlin; Ernst Hickl; Hans-Dieter Beckhaus; Christoph Rüchardt; Sergei I. Kozhushkov; Rainer Haag; Roland Boese; Jordi Benet-Bucholz; Karsten Nordhoff; Armin de Meijere (2002). "Thermochemical and X-ray Crystallographic Investigations of Some (CH)₁₀ Hydrocarbons: Basketene, Nenitzescu's Hydrocarbon, and Snoutene". European Journal of Organic Chemistry. 2002 (14). Wiley VCH: 2280–7. doi:10.1002/1099-0690(200207)2002:14<2280::AID-EJOC2280>3.0.CO;2-R. Archived from the original on 2013-01-05. Retrieved 2009-11-23.

[synth-2] Smit, William A.; Bochkov, Alekseĭ Feodosʹevich; Caple, Ron (1998). Organic synthesis: the science behind the art. Royal Society of Chemistry. p. 184. ISBN 978-0-85404-544-0. Retrieved 2008-12-10.

[3] Allred, Evan L.; Beck, Boyd R. (1973). "Concurrent thermolysis and photolysis of basketene. Formation and the interrelation of some new (CH)₁₀ isomers". Journal of the American Chemical Society. 95 (7): 2393. doi:10.1021/ja00788a065.

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