It is well-known that under thermodynamic conditions 5a-3-keto steroids such as 3- cholestanone enolize predominantly toward C-2, while the 5P-isomers enolize toward C-4. It has been tacitly assumed that 2-decalones, bicyclic analogues of the steroids, show similar selectivity. In a systematic investigation of the direction of enolization of 2-decalones, 11 bicyclic ketones plus two representative steroids have been converted to the ...
