Acid-catalysed acylations of bicyclo[3.3.1]nonan-2,6-diones: A novel preparation of the adamantane skeleton |
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| Authors: | P.H. Mccabe C.R. Nelson W. Routledge |
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| Affiliation: | Department of Chemistry, University of Glasgow, GlasgowG12 8QQ, Scotland |
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| Abstract: | The acid-catalysed acylations of bicyclo[3.3.1]nonan-2,6-dione 1 and its 9-thia-2 and 9-oxa-3 analogues with Ac2O are described. At high acidity, C-acylation is favoured over O-acylation and for 1 and 2 intramolecular aldol condensation occurs with the formation of adamantanes 18 and 19 and 2-thiaadamantanes 15 and 16. These results are compared with alternative acylations of 2 using 2-acetoxypropene, (PhCO)2O and acid halides. |
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