Sumanene
Sumanene is a polycyclic aromatic hydrocarbon and of scientific interest because the molecule can be considered a fragment of buckminsterfullerene.Unlike fullerene, sumanene has benzyl positions which are available for organic reactions.The structure of Sumanene can be inferred from oxidation of 1,5,9-trimethyltriphenylene but the first practical synthesis starts from norbornadiene.[3] The 6 hub carbon atoms are pyramidalized by 9° and the molecule displays considerable bond alternation (138.1 to 143.1 pm).[4] Electron transport properties have been investigated [5][6] as well as carbon NMR[7] Sumanene derivatives [8] such as naphtosumanene [9] and trisialsumanene [10][11] have been described.
Preferred IUPAC nameCAS NumberChemSpiderPubChemCompTox DashboardSMILESChemical formulaMolar massstandard statepolycyclic aromatic hydrocarbonmoleculebuckminsterfullerenesunflowerSanskritbenzenecyclopentadienefullerenebenzylorganic reactionsoxidationtriphenylenenorbornadienestannanen-butyllithiumdibromoethaneUllmann reactiontandemring-opening metathesisring-closing metathesisGrubbs' catalystpicometerspyramidalizedinversion barriercorannuleneprotont-butyl lithiumcarbanionnucleophileelectrophiletrimethylsilyl chloridetrimethylsilylcarbon NMRinherent chiralityGoverdhan MehtaChemical CommunicationsScienceJ. Am. Chem. Soc.Polycyclic aromatic hydrocarbonsButaleneAzuleneNaphthaleneAcenaphtheneAcenaphthyleneAnthraceneFluorenePhenalenePhenanthreneBenz[a]anthraceneBenzo[a]fluoreneBenzo[c]fluoreneBenzo[c]phenanthreneChryseneFluoranthenePyreneTetraceneTricyclobutabenzeneBenz[e]acephenanthryleneBenzopyreneBenzo[a]pyreneBenzo[e]pyrene6H-Benzo[cd]pyrene(Olympicene)Benzo[a]fluorantheneBenzo[b]fluorantheneBenzo[j]fluorantheneBenzo[k]fluoranthenetrans-BicaliceneDibenz[a,h]anthraceneDibenz[a,j]anthracenePentacenePerylenePiceneTetraphenyleneAnthanthreneBenzo[ghi]peryleneDibenzopyrenesHexaceneTrianguleneZethreneCoroneneDicoronyleneDiindenoperyleneHeptaceneHexabenzocoroneneHexa-cata-KekuleneOvaleneRubiceneRubreneSuperphenaleneTrinaphthyleneTruxeneCirculeneCyclaceneHelicenePhenacene