Synthesis and properties of unusual π-networks : Cycloocta[1,2,3,4]-def]benzo[3,4]cyclobuta[6,7[biphenylene

The title compound, an example of a hydrocarbon containing three linearly fused 4n-membered rings, has been synthesized and characterized as a thermally stable species possessing no unusual chemical reactivity. Despite the presence of these conventionally antiaromatic structural units this hydrocarbon is predicted to have a net diamagnetic ring current. The NMR results, which are discussed in some detail, are shown to be consistent with this expectation. The impact of this result on the NMR criterion of aromaticity is discussed briefly.