The π-route to substituted adamantanes. Part I

Abstract

Rearrangement reactions whereby 4-oxahomoadamantan-5-one gives predominantly 4_ax-hydroxyadamantan-2-one in hot 50% sulphuric acid and predominantly 4_ax-methylsulphonyloxyadamantan-2-one in hot methane-sulphonic acid, and adamantanone with sodium azide gives 4_eq-methylsulphonoxyadamantan-2-one in cold methanesulphonic acid, are discussed in terms of π-route cyclisations, thermodynamically controlled in the first two cases and kinetically controlled in the third.