{{More citations needed|date=December 2024}} {{chembox | verifiedrevid = 461339265 | ImageFileL1 = Basketeen.png | ImageSizeL1 = 120 | ImageAltL1 = Skeletal formula | ImageFileR1 = Basketene-3D-balls.png | ImageSizeR1 = 120 | ImageAltR1 = Ball-and-stick model | PIN = Pentacyclo[4.4.0.0<sup>2,5</sup>.0<sup>3,8</sup>.0<sup>4,7</sup>]dec-9-ene | OtherNames = Bishomocubene |Section1={{Chembox Identifiers | Abbreviations = | CASNo_Ref = {{cascite|correct|??}} | CASNo = 5603-34-9 | EINECS = | StdInChI = 1S/C10H10/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h1-10H | StdInChIKey = LXQOIQYQFRKBLV-UHFFFAOYSA-N | PubChem = 138538 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 122156 | SMILES = C2=CC5C1C4C3C1C2C3C45 | InChI = InChI=1/C10H10/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h1-10H | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | Formula = C<sub>10</sub>H<sub>10</sub> | MolarMass = 130.186 g/mol | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} }}
'''Basketene''' (IUPAC name: pentacyclo[4.4.0.0<sup>2,5</sup>.0<sup>3,8</sup>.0<sup>4,7</sup>]dec-9-ene<ref name="thermo"> {{cite journal | last = Verevkin | first = Sergei P. | author2=Martin Kümmerlin |author3=Ernst Hickl |author4=Hans-Dieter Beckhaus |author5=Christoph Rüchardt |author6=Sergei I. Kozhushkov |author7=Rainer Haag |author8=Roland Boese |author9=Jordi Benet-Bucholz |author10=Karsten Nordhoff |author11=Armin de Meijere | year = 2002 | title = Thermochemical and X-ray Crystallographic Investigations of Some (CH)<sub>10</sub> Hydrocarbons: Basketene, Nenitzescu's Hydrocarbon, and Snoutene | journal = European Journal of Organic Chemistry | volume = 2002 | issue = 14 | pages = 2280–7 | publisher = Wiley VCH | doi = 10.1002/1099-0690(200207)2002:14<2280::AID-EJOC2280>3.0.CO;2-R }} </ref>) is an organic compound with the formula C<sub>10</sub>H<sub>10</sub>. It is a polycyclic alkene and the dehydrogenated version of basketane, which was named for its structural similarity to a basket. Due to its hydrocarbon composition and unique structure, the chemical compound is of considerable interest to those examining energy surfaces of these (CH)<sub>10</sub> cage molecules and what possible factors influence their minima.<ref name="Allred and Evan">{{cite journal |last1=Allred |first1=Evan L. |last2=Beck |first2=Boyd R. |title=Concurrent thermolysis and photolysis of basketene. Formation and the interrelation of some new (CH)10 isomers |journal=Journal of the American Chemical Society |date=1973 |volume=95 |issue=7 |doi=10.1021/ja00788a065}}</ref> Additionally, the complex structure of this compound has intrigued researchers studying the chemistry of highly strained ring systems .<ref>{{cite journal |last1=Gassman |first1=Paul G. |last2=Yamaguchi |first2=Ryohei |title=1,8-Bishomocubane |journal=Journal of Organic Chemistry |date=1978 |volume=43 |issue=24 |doi=10.1021/jo00418a028}}</ref> Basketene and its family of derivatives also have important chemical and physical properties. These molecules all tend to have a high standard enthalpy of formation, combined with their high density, leading to possible uses in explosives.<ref name="HCA">{{cite journal |last1=Aydinli |first1=Betül |last2=Çelik |first2=Murat |last3=M. Serdar |first3=Gültekin |last4=Uzun |first4=Orhan |last5=Balci |first5=Metin |title=Controlled Synthesis of Substituted Benzobasketene Derivatives |journal=Helvetica Chimica Acta |date=2003 |volume=86 |doi=10.1002/hlca.200390276|hdl=11511/56422 |hdl-access=free }}</ref>
==Synthesis== Basketene has been synthesized as follows. First cyclooctatetraene ('''1''') undergoes thermal, electrocyclic isomerization (to '''2'''), followed by a Diels–Alder reaction with maleic anhydride ('''3'''). [2 + 2] photochemical cycloaddition ('''4''' to '''5''') closes the cage structure, which sodium carbonate hydrolyzes (to '''6'''); lead(IV) acetate in pyridine then decarboxylates oxidatively to basketene ('''7''').<ref>{{cite book |last1=Smit |first1=W. A. |last2=Bochkov |first2=A. F. |last3=Caple |first3=R. |title=Organic Synthesis: The Science Behind the Art |date=1998 |publisher=The Royal Society of Chemistry |page=184}}</ref> :600px|Total Synthesis of Basketene
==Reactions== Basketene and other cage molecules are important for discovering and testing new concepts of bonding and reactivity.<ref name="HCA" /> Oxidizing basketene with osmium tetroxide selectively cleaves the alkene to two carboxylic acid groups; ketonization then gives a cubane precursor.<ref>{{Cite journal |last=Chin |first=Clinton G. |last2=Cuts |first2=Harold W. |last3=Masamune |first3=Satoru |date=1966 |title=Strained systems: cubane |url=https://xlink.rsc.org/?DOI=c19660000880 |journal=Chemical Communications |language=en |issue=23 |pages=880 |doi=10.1039/c19660000880 |issn=0009-241X|url-access=subscription }}</ref>
Basketene also undergoes a number of different rearrangements.
===Rearrangements=== Heating Basketene alone produces Nenitzescu’s Hydrocarbon. The reaction proceeds through a reverse Diels-Alder intermediate in order to give '''8''' at 110 ˚C. From '''8''', a 3,3 shift occurs to give Nenitzescu's hydrocarbon ('''9''').<ref name="Allred and Evan" /> :480px|Basketene Rearrangement into NHC
The intermediate '''8''' can be captured by trapping it as a 1:1 adduct with maleic anhydride.{{Citation needed|date=June 2025}}
Basketene can also undergo the following thermal and photochemical rearrangement reactions. The photo-induced conrotary opening of '''8''' gives cis,cis,trans-cyclooctatriene (10). Furthermore, the photo-rearrangement of '''10''' provides the derivative '''11'''. '''11''' will undergo a direct photochemical (2+2) cyclization closure to '''12'''.{{Citation needed|date=June 2025}} :540px|Basketene Thermal and Photochemical Rearrangements
Basktene also rearranges into snoutene when in solution with Silver nitrate<ref name=thermo/> :310px|Basktene with Silver Nitrate into Snoutin
{{Commons category}}
==References== <references/>
Category:Polycyclic nonaromatic hydrocarbons Category:Alkene derivatives Category:Pentacyclic compounds Category:Cyclohexenes Category:Cyclobutanes