Syntheses and Properties of Allene・Cumulene Compounds Connecting with Non-benzenoid Aromatics

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The purpose of our project is to synthesize cumulated compounds which possess conjugate system with non-benzenoid aromatics such as cycloheptatrienylidene, cyclopentadienylidene or cyclopropenylidenes, and to investigate chemical and physical properties of those novel conjugate compounds.For this, arylcycloheptatrienylidene-ethenes were synthesized and it was found that those compounds readily gave three different kinds of dimer which properties were also investigated.Some cyclopentadienylideneethenes have been reported, but their thermal unstability did not allow detailed studies. We found that substitution of hydrogen atom at the C-1 position by bromine atom makes those system stable and some cyclopentadienylidene-ethenes were obtained. Several physical properties and thermal dimerization reactions of the cyclopentadienylidenes including some arylallene derivatives were investigated. As the results, the dimerization mechanisms are established.Syntheses of cyclopropenylidene derivatives have not been succeeded yet. Further attempts will be made in feature. Additional research has been done about reactions of diphenylcyclopropenone with hydrazines and multiple reactivities of this system has been explored to give pyrazole derivatives via cinnamhydrazides and also styrilformazan derivatives.Several pyrene derivatives and benz[a]indeno[1,2,3-cd]azulene derivatives were synthesized and their chemical properties were investigated as new materials for complex formation and for arylallene derivatives' syntheses.