Triptycene

• 9,10- dihydro- 9, 10 [1 ', 2' ] benzenoanthracen
• Tribenzobicyclo [2.2.2 ] octatriene
• NSC122926
• 9,10 [1 ', 2' ] Benzenoanthracen

Colourless crystals

256 ° C

Template: Infobox chemical / molecular formula search available

Triptycene belongs to the class of aromatic hydrocarbons, the basic framework consists of the barrelene. It is the formal product of a Diels- Alder reaction of anthracene with 1,2- benzyne, a Arin. The compound has a paddle wheel configuration with D3h symmetry. The hydrocarbon backbone is very rigid, can be so triptycene and triptycene derivatives, such as Triptycenchinon used in organic compounds as a molecular scaffold in the synthesis of certain molecular motors or used as a specific ligand systems for eg hydrocyanation.

History

Paul D. Bartlett and co-workers published the synthesis in 1942 and named it after "The triptych of antiquity ", translated " The Triptych of Antiquity", a book consisting of three to an axle mounted together pages.

Production and representation

The original synthesis of the triptycene was seven steps, starting from anthracene, and p-benzoquinone. In the laboratory, triptycene of anthracene and anthranilic acid can be produced. Here, the reactive and short-lived Benzyn is produced by amyl nitrite and anthranilic acid, which reacts in situ with anthracene by a Diels -Alder reaction on the central benzene ring of the anthracene to the triptycene.