Send to

Choose Destination
ChemistryOpen. 2018 Jan 12;7(1):111-114. doi: 10.1002/open.201700196. eCollection 2018 Jan.

Regiochemical Control in Triptycene Formation-An Exercise in Subtle Balancing Multiple Factors.

Author information

Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Universität Bielefeld, Fakultät für Chemie Universitätsstraße 25 33615 Bielefeld Germany.


Reactions between 1,8-dichloroanthracenes with substituents in position 10 and ortho-chloroaryne afford mixtures of 1,8,13- (syn) and 1,8,16-trichlorotriptycenes (anti). The syn/anti ratio is dependent on these substituents. Electropositive substituents like SiMe3 and GeMe3 lead to preferred formation of the syn-isomer, whereas CMe3 groups exclusively afford the anti-isomer. Different quantum chemical calculations including location of transition states give conflicting results, but indicate the importance of dispersion forces for an at least qualitative prediction of results. The syn-trichlorotriptycenes with SiMe3 and GeMe3 substituents were characterized by using NMR spectroscopy, mass spectrometry, and X-ray diffraction experiments.


anthracenes; cycloaddition; dispersion; solid-state structures; triptycenes

Supplemental Content

Full text links

Icon for Wiley Icon for PubMed Central
Loading ...
Support Center