Abstract

The syntheses of a number of polycyclic systems containing potential cyclobutadiene rings are described. The main route to these compounds involved a bis-Wittig reaction with a compound containing a four-membered ring, but alternative routes are also discussed. The properties of the compounds are described, and it is shown that, in those cases in which delocalization occurs, the nuclear magnetic resonance spectra are consistent with those systems having a paratropic contribution from the four-membered ring. In the case of 2-thianorbiphenylene, the paratropic component can be removed by oxidation to 2-thianorbiphenylene 2,2-dioxide. The electronic spectra of biphenylene, 2-thianorbiphenylene, and tetraphenyl-2,5-dithiabisnorbiphenylene were found to be similar.

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