Triptycene
From Wikipedia, the free encyclopedia
| Triptycene | |
|---|---|
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| Identifiers | |
| CAS number | 477-75-8 |
| SMILES | C12=CC=CC=C1C3C5=C (C=CC=C5)C2C4=C3C=CC=C4 |
| Properties | |
| Molecular formula | C20H14 |
| Molar mass | 254.33 g/mol |
| Melting point |
252 - 256 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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]
[edit] References
- ^ Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article
- ^ Unidirectional rotary motion in a molecular system T. Ross Kelly, Harshani De Silva and Richard A. Silva Nature 1999, 401, 150-152. Abstract
- ^ Highly Selective Hydrocyanation of Butadiene toward 3-Pentenenitrile Bini, L.; Muller, C.; Wilting, J.; von Chrzanowski, L.; Spek, A. L.; Vogt, D. J. Am. Chem. Soc.; (Communication); 2007; 129(42); 12622-12623. doi:10.1021/ja074922e
- ^ 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
