Triptycene
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| Identifiers | |
|---|---|
477-75-8  | |
| 3D model (Jmol) | Interactive image |
| ECHA InfoCard | 100.006.837 |
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| Properties | |
| C20H14 | |
| Molar mass | 254.33 g·mol−1 |
| Melting point | 252 to 256 °C (486 to 493 °F; 525 to 529 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Triptycene is an aromatic hydrocarbon, the simplest iptycene molecule with the formula C2H2(C6H4)3. It is a white solid that is soluble in organic solvents. The compound has a paddlewheel configuration with D3h symmetry. Several substituted triptycenes are known. Barrelenes are structurally related.
Synthesis
The parent triptycene was first prepared in 1942 by a multistep method.[1] It can also be prepared in one step in moderate yields (28%) from the Diels-Alder reaction of anthracene and benzyne.[2] In this method, benzyne is generated by the reaction of magnesium in the presence of 2-bromofluorobenzene.
Derivatives and applications
The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones[3] are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors [4] or as a ligand for example in this hydrocyanation:[5]
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 triptycene scaffold.
References
- ↑ Bartlett, Paul D.; Ryan, M. Josephine; Cohen, Saul G. (1942). "Triptycene1 (9,10-o-Benzenoanthracene)". J. Am. Chem. Soc. 64: 2649. doi:10.1021/ja01263a035.
- ↑ Wittig, George (1959). "Triptycene". Org. Synth. 39: 75. doi:10.15227/orgsyn.039.0075.
- ↑ Spyroudis S, Xanthopoulou N (2003). "Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione" (pdf). Arkivoc. 2003 (vi): 95–105.
- ↑ Kelly TR, De Silva H, Silva RA (September 1999). "Unidirectional rotary motion in a molecular system". Nature. 401 (6749): 150–152. doi:10.1038/43639. PMID 10490021.
- ↑ 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): 12622–12623. doi:10.1021/ja074922e. PMID 17902667.