The adamantyl cation with acetylene in sulphuric acid is shown to give an intermediate sulphate which is the precursor of 1-adamantylacetaldehyde or of 1-methylhomoadamantan-2-one, depending on the amount of water present: with carbon monoxide a retrogression is observed giving adamantane-1-carboxylic acid, and in the presence of bromide the acetylene reaction leads to adamantyl methyl ketone.
D. R. Kell and F. J. McQuillin, J. Chem. Soc. D, 1970, 599 DOI: 10.1039/C29700000599
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