Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors

Jan Hendrik Lamm, Yury V. Vishnevskiy, Eric Ziemann, Beate Neumann, Hans Georg Stammler, Norbert W. Mitzel

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


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.

Original languageEnglish
Pages (from-to)111-114
Number of pages4
Issue number1
StatePublished - 1 Jan 2018
Externally publishedYes


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

ASJC Scopus subject areas

  • General Chemistry


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