Triptycene

Structural formula
General
Surname	Triptycene
other names	9,10-dihydro-9,10 [1 ', 2'] - benzenoanthracene; Tribenzobicyclo [2.2.2] octatriene; NSC122926; 9.10 [1 ', 2'] - Benzenoanthracene;
Molecular formula	C 20 H 14
Brief description	Colorless crystals
External identifiers / databases
EC number	207-519-3
ECHA InfoCard	100.006.837
PubChem	92764
Wikidata	Q411264
properties
Molar mass	254.33 g mol −1
Physical state	firmly
Melting point	256 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triptycene belongs to the class of aromatic hydrocarbons, the basic structure of which consists of the barrel . It is the formal product of a Diels-Alder reaction of anthracene with 1,2-didehydrobenzene, an aryne . The compound has a paddle wheel configuration with D _3h - symmetry . The hydrocarbon framework is extremely rigid, so that triptycene and triptycene derivatives, such as triptycenequinone, can be used in organic compounds as a molecular framework in the synthesis of certain molecular motors or as special ligand systems for, for example, hydrocyanation reactions .

history

Paul D. Bartlett and colleagues published the synthesis in 1942 and named it after "The triptych of antiquity", translated as "The Triptych of Antiquity", a book consisting of three pages attached to an axis.

Extraction and presentation

The original synthesis of triptycene took place in seven steps, starting with anthracene and p -benzoquinone . Triptycene can be produced from anthracene and anthranilic acid in the laboratory . The reactive and short-lived benzyne is produced using amyl nitrite and anthranilic acid, which reacts in situ with anthracene after a Diels-Alder reaction on the central benzene ring of the anthracene to form triptycene.

Individual evidence

↑ ^a ^b entry on triptycene. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
↑ ^a ^b Data sheet Triptycene, 98% from Sigma-Aldrich , accessed on February 27, 2013 ( PDF ).
↑ Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article (PDF; 186 kB).
↑ Kelly TR, De Silva H, Silva RA: Unidirectional rotary motion in a molecular system . In: Nature . 401, No. 6749, September 1999, pp. 150-152. doi : 10.1038 / 43639 . PMID 10490021 .
↑ Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D: Highly selective hydrocyanation of butadiene toward 3-pentenenitrile . In: J. Am. Chem. Soc. . 129, No. 42, October 2007, pp. 12622-12623. doi : 10.1021 / ja074922e . PMID 17902667 . In this reaction, the substrate is 1,3-butadiene , the reactant is acetone cyanohydrin , the catalyst Ni (cod) 2 and the ligand is a bidentate organophosphine with a large grip angle on a triptycene framework.

[RÖMPP_Online-1] try on triptycene. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.

[Sigma-2] Data sheet Triptycene, 98% from Sigma-Aldrich , accessed on February 27, 2013 ( PDF ).

[3] Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article (PDF; 186 kB).

[4] Kelly TR, De Silva H, Silva RA: Unidirectional rotary motion in a molecular system . In: Nature . 401, No. 6749, September 1999, pp. 150-152. doi : 10.1038 / 43639 . PMID 10490021 .

[5] Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D: Highly selective hydrocyanation of butadiene toward 3-pentenenitrile . In: J. Am. Chem. Soc. . 129, No. 42, October 2007, pp. 12622-12623. doi : 10.1021 / ja074922e . PMID 17902667 . In this reaction, the substrate is 1,3-butadiene , the reactant is acetone cyanohydrin , the catalyst Ni (cod) 2 and the ligand is a bidentate organophosphine with a large grip angle on a triptycene framework.