Novel cyclic 1, 2, 3, 4, 5-hexapentaene compounds were synthesized from cyclic diyne-diol IX via diallene-dibromide X in order to study transannular electronic interaction. A diallene- dibromide Xc-I obtained from a diyne-diol isomer IXc-I was debrominated with active zinc to give cyclic hexapentaene IIc, whereas the other diallene-dibromide Xc-II derived from the second diyne-diol isomer IXc-II was not. The X-ray crystallographic analysis of the ...