Monodeoxygenation of spiro adamantane-1,2-dioxetanes induced by aminium salt

Abstract

The reactions of 4,4-dimethylspiro[adamantane-2,3′-[1,2]-dioxetane] (1a) and biadamantylidene-1,2-dioxetane (2a) in dichloromethane, at different reaction temperatures, with tris-(2,4-dibromophenyl) aminium hexachloroantimonate A afford high yields of the rearranged ketones 2-methyladamantyl-methyl ketone (3) and spiro[adamantane-2,4′-homoadamantan-5′-one] (8), respectively. A cation radical monodeoxygenation process is suggested.