Gas-phase pyrolytic formation and dimerization of benzocyclobutenes: Synthesis of [24](1,2,4,5) cyclophane
Abstract
Gas-phase pyrolysis of benzocyclobutenes in a nitrogen stream at 450°C is a convenient efficient method for preparing dibenzocyclooctadienes. Application of this method to benzo[1,2;4,5]dicyclobutene gives [24](1,2,4,5)cyclophane directly. However, under the same reaction conditions, 3,6-dimethylbenzo[1,2;4,5]dicyclobutene gives the open [2.2]orthocyclophane derivative, whose structure has been established by x-ray crystallographic analysis of the corresponding iron complex.
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