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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

1
Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Universität Bielefeld, Fakultät für Chemie Universitätsstraße 25 33615 Bielefeld Germany.

Abstract

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.

KEYWORDS:

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

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