The fourfold clamped title hydrocarbon 5, the biphenylene unit of which is strongly deformed out of plane, was obtained in 13% yield via sulfone pyrolysis; the X-ray analysis demonstrates that the framework of the biphenylene unit is bent out of planarity up to 18.7° due to transannular repulsioon, whereas the C–C bonds of the four ethano bridges are elongated compared with reference compounds.
K. Saitmacher, J. E. Schulz, M. Nieger and F. Vögtle, J. Chem. Soc., Chem. Commun., 1992, 175 DOI: 10.1039/C39920000175
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