Reaction of 1,3-Dihaloadamantanes with Nitric Acid

1,3-Dibromoadamantane derivatives reacted with fuming nitric acid to give mixtures of products with a 2-oxaadamantane skeleton. 1,3-Diiodoadamantane analogs under similar conditions were converted only to the corresponding 1,3-dinitroxyadamantanes. A preparative procedure has been developed for the synthesis of 3-(bromomethyl)-5,7-dimethyl-2-oxaadamantan-1-ol from 1,3-dibromo-5,7-dimethyladamantane. Due to the presence of several functional groups, the synthesized compounds can be used as starting materials for obtaining derivatives exhibiting a broad spectrum of biological activity.