To use all functions of this page, please activate cookies in your browser.
my.chemeurope.com
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
Sumanene
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.[1] 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. Additional recommended knowledgeOrganic synthesisThe structure of Sumanene can be inferred from oxidation of 1,5,9-trimethyltriphenylene but the first practical synthesis starts from norbornadiene.[2] 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 groups 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. PropertiesSumanene is a bowl shaped molecule with a bowl depth of 1.18 angstroms (118 picometers).[3] The 6 hub carbon atoms are pyramidalized by 9° and the molecule displays considerable bond alternation (138.1 to 143.1 pm). Sumanene also experiences bowl-to-bowl inversion with an inversion barrier of 19.6 kcal/mol (82 kJ/mol) at 140 °C which is much higher than that found for its corannulene cousin. Like any benzylic proton, the sumanene protons can be abstracted by a strong base such as t-butyl lithium to form the sumanene mono carbanion. This strong nucleophile can react with an electrophile such as trimethylsilylchloride to the trimethylsilyl derivative. References
Categories: Geodesic polyarenes | Polycyclic aromatic hydrocarbons |
||||||||||||||||||||||
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sumanene". A list of authors is available in Wikipedia. |