Synthetic Study of [0^4] Paracyclophane Using Valence-Bond Isomerization of Dewar Benzenes

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In the present study, a novel belt-type molecule, [0^4] paracyclophane 1, composed of bent benzene rings was designed and attempted to be synthesized by using valence-bond isomerization of Dewar benzenes in the final step.In 1996,8,10-dichloro-3,5-dioxobicyclo [5.2.2] undeca-8,10-diene 2 was synthesized in four steps from dimethyl acetylenedicarboxylate as a new Dewar benzene building block and its molecular structure and chemical reactivity were examined.In 1997, synthesis of butadiene-expanded [0^6] paracyclophane 3 from the building block 2 was examined and the corresponding oligo (Dewar) benzene precursor was successfully synthesized. Model compound for 3, in which four paraphenylene units in 3 are replaced by metaphenylene units, was also synthesized.