Triptycene

Synthesis

The parent triptycene was first prepared in 1942 by a multistep method. It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne. In this method, benzyne is generated by the reaction of magnesium and 2-bromofluorobenzene.

Derivatives and applications

The hydrocarbon framework is very rigid and triptycene derivatives such as triptycene quinones are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors or ligands.

For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene. The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.

References

References

1. (2010). "Triptycene Derivatives: Synthesis and Applications". Chemistry Letters.
2. (1942). "Triptycene (9,10-''o''-Benzenoanthracene)". J. Am. Chem. Soc..
3. (1959). "Triptycene". Org. Synth..
4. (2003). "Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione". [[Arkivoc]].
5. (September 1999). "Unidirectional rotary motion in a molecular system". Nature.
6. (October 2007). "Highly selective hydrocyanation of butadiene toward 3-pentenenitrile". J. Am. Chem. Soc..