Syntheses of functional molecules using highly strained sp-carbon atoms in unsaturated cyclic organometallic compounds

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We studied on the synthesis, structure and reactivity on conjugated five-membered alkyne complexes derived from group 4 metals and cumulene derivatives. We also investigated five-membered cyclic allenes that are formed from conjugated enynes on the property of highly strained sp carbon in the cyclic unsaturated compounds. It is difficult to isolate one of the isomers of E/Z-[5]cumulenes because of low barrier for isomerization. We succeeded in isolation of the E-isomer and trapping the Z-isomer as a metal complex. Haptotropic interconversion between cyclic structure and eta2-coordination was also examined and the effect of steric environment of the substituents were found. We have found facile preparative method of five-membered cyclic allene from conjugated enyne.