Triptycene

Triptycene
Identifiers
CAS number 477-75-8 Y
Jmol-3D images Image 1
Properties
Molecular formula C20H14
Molar mass 254.33 g/mol
Melting point

252 - 256 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

  1. ^ Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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

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