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sumanene
Sign in to saveSumanene is a polycyclic aromatic hydrocarbon and of scientific interest because the molecule can be considered a fragment of buckminsterfullerene. Due to this connection and also its bowl shape, Sumanene is also known as a buckybowl. Suman means "flower" in both Hindi and Sanskrit. The core of the arene is a benzene ring and the periphery consists of alternating benzene rings (3) and cyclopentadiene rings (3). Unlike fullerene, sumanene has benzyl positions which are available for organic reactions.
Chemical data
- Formula
- C21H12
- Molecular weight
- 264.3 g/mol
- IUPAC name
- heptacyclo[12.6.1.04,19.06,18.09,17.011,16.015,20]henicosa-1(20),2,4(19),6(18),7,9(17),11(16),12,14-nonaene
- SMILES
- C1C2=C3C4=C(CC5=C4C6=C(CC7=C6C3=C1C=C7)C=C5)C=C2
- InChIKey
- WOYKPMSXBVTRKZ-UHFFFAOYSA-N
- XLogP
- 4.9
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 264.0939
Show 3 more facts
- chemical formula
- C₂₁H₁₂
- canonical SMILES
- C1C2=C3C4=C(CC5=C4C6=C(CC7=C6C3=C1C=C7)C=C5)C=C2
- Commons category
- Sumanene
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Organic synthesis
- Properties
- Derivatives
- See also
- References
Sumanene is a polycyclic aromatic hydrocarbon and of scientific interest because the molecule can be considered a fragment of buckminsterfullerene. Due to this connection and also its bowl shape, Sumanene is also known as a buckybowl. Suman means "flower" in both Hindi and Sanskrit. The core of the arene is a benzene ring and the periphery consists of alternating benzene rings (3) and cyclopentadiene rings (3). Unlike fullerene, sumanene has benzyl positions which are available for organic reactions.
== Organic synthesis == 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. An Ullmann reaction of this stannane with CuTC affords the benzene core. The methylene bridges () 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. Sumanene synthesis
Excerpted from Wikipedia’s “sumanene” article, available under the CC BY-SA 4.0 licence.