Acid-catalysed acylations of bicyclo[3.3.1]nonan-2,6-diones: A novel preparation of the adamantane skeleton |
| |
| Authors: | PH Mccabe CR Nelson W Routledge |
| |
| Institution: | Department of Chemistry, University of Glasgow, GlasgowG12 8QQ, Scotland |
| |
| Abstract: | The acid-catalysed acylations of bicyclo3.3.1]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. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
