The reaction of cyclo-octanone semicarbazone (2) with SeO2 leads to cyclo-octeno-1,2,3-selenadiazole (3) from which, on heating to 170–220°, cyclo-octyne (5), the lowest stable cycloalkyne, can be prepared in good yields.
H. Meier and I. Menzel, J. Chem. Soc. D, 1971, 1059 DOI: 10.1039/C29710001059
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