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

Article abstract of DOI:10.1016/S0040-4020(98)00375-5

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.