3-Ethynyltricyclo[3.3.1.03,7]nonane is conveniently prepared from adamantanone, via an anomalous alkylidenecarbene rearrangement, by flash vacuum thermolysis of 5-adamantylidene-2,2-dimethyl-1,3-dioxane-4,6-dione.
J. Scharp and U. E. Wiersum, J. Chem. Soc., Chem. Commun., 1983, 629 DOI: 10.1039/C39830000629
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