Triptycene
From Wikipedia, the free encyclopedia
| Triptycene | |
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| Identifiers | |
| CAS number | 477-75-8  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C20H14 |
| Molar mass | 254.33 g/mol |
| Melting point |
252 - 256 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Triptycenes are a class of aromatic hydrocarbons. The parent compound triptycene is the Diels-Alder reaction product of anthracene and benzyne. The compound has a paddlewheel configuration with D3h symmetry. Barrelenes are conceptually related compounds. The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones [1] are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors [2] or as a ligand for example in this hydrocyanation:[3][4]
[edit] References
- ^ Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article
- ^ Kelly TR, De Silva H, Silva RA (September 1999). "Unidirectional rotary motion in a molecular system". Nature 401 (6749): 150–2. doi:10.1038/43639. PMID 10490021. http://www.nature.com/nature/journal/v401/n6749/abs/401150a0.html. Retrieved 2008-07-16.
- ^ Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D (October 2007). "Highly selective hydrocyanation of butadiene toward 3-pentenenitrile". J. Am. Chem. Soc. 129 (42): 12622–3. doi:10.1021/ja074922e. PMID 17902667.
- ^ In this reaction the substrate is butadiene,the reagent acetonecyanohydrine, the catalyst Ni(cod)2 and the ligand a bidentate organophosphine with a large bite angle on a trypticene scaffold
