Treatment of adamantan-1-ol in sulphuric acid with acetylene leads to 1-adamantylacetaldehyde or 1-adamantyl methyl ketone as major product (together with 1-methylhomoadamantan-2-one), depending on the experimental conditions (acid concentration and reaction time). The reactions of the adamantyl, diphenylmethyl, and norbornyl cations with acetylene and substituted acetylenes have been examined.
D. R. Kell and F. J. McQuillin, J. Chem. Soc., Perkin Trans. 1, 1972, 2100 DOI: 10.1039/P19720002100
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