Sumanene

Sumanene
Names


IUPAC name 4,7-Dihydro-1H-tricyclopenta[def,jkl,pqr]triphenylene
Identifiers
CAS Number	151253-59-7^Y
3D model (JSmol)	Interactive image
ChemSpider	9348199^N
PubChem CID	11173107
InChI InChI=1S/C21H12/c1-2-11-8-13-5-6-15-9-14-4-3-12-7-10(1)16-17(11)19(13)21(15)20(14)18(12)16/h1-6H,7-9H2^N Key: WOYKPMSXBVTRKZ-UHFFFAOYSA-N^N InChI=1/C21H12/c1-2-11-8-13-5-6-15-9-14-4-3-12-7-10(1)16-17(11)19(13)21(15)20(14)18(12)16/h1-6H,7-9H2 Key: WOYKPMSXBVTRKZ-UHFFFAOYAE
SMILES C16=C5C4=C3C2=C1C7=CC=C2CC3=CC=C4CC5=CC=C6C7
Properties
Chemical formula	C₂₁H₁₂
Molar mass	264.32
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Sumanene is a polycyclic aromatic hydrocarbon and of scientific interest because the molecule can be considered a fragment of buckminsterfullerene. Suman means "sunflower" in both Hindi and Sanskrit. The core of the arene is a benzene ring and the consists of alternating benzene rings (3) and cyclopentadiene rings (3). 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. Norbornadiene is converted into a stannane by action of n-butyllithium, dibromoethane and tributyltinchloride. A Ullmann reaction of this stannane with CuTC affords the benzene core. The methylene bridges (-CH
2-) created in this conversion then migrate in a tandem ring-opening metathesis and ring-closing metathesis by the Grubbs' catalyst. The final structure is obtained by oxidation by DDQ.