Synthesis, x-ray structure, and properties of a tetrabenzannelated 1,2,4,5-cyclophane

Michael Brettreich, Michael Bendikov, Sterling Chaffins, Dmitrii F. Perepichka, Olivier Dautel, Hieu Duong, Roger Helgeson, Fred Wudl

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)


Highly strained but thermally stable: Tetrabenzocyclophane 1, which was obtained in a four-step synthesis by two Diels - Alder addition reactions (see scheme) sublimes at high temperature, rather than decomposing. The distorted aromatic rings are more reactive with tetracyanoethylene than those in [2.2]paracyclophane. Another consequence of heightened strain is a bathochromic shift of the cyclophane band to 330 nm, the longest wavelength absorption for this band to date.

Original languageEnglish
Pages (from-to)3688-3691
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number19
Publication statusPublished - Oct 4 2002


  • Cycloaddition
  • Cyclophanes
  • Density functional calculations
  • Electrochemistry
  • Strained molecules

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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