Triptycene
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| Identifiers | |
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3D model (JSmol)
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| ECHA InfoCard | 100.006.837 |
CompTox Dashboard (EPA)
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| Properties | |
| C20H14 | |
| Molar mass | 254.33 g/mol |
| Melting point | 252 - 256 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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 (1999). "Unidirectional rotary motion in a molecular system". Nature. 401 (6749): 150–2. doi:10.1038/43639. PMID 10490021. Retrieved 2008-07-16.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D (2007). "Highly selective hydrocyanation of butadiene toward 3-pentenenitrile". J. Am. Chem. Soc. 129 (42): 12622–3. doi:10.1021/ja074922e. PMID 17902667.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ 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