Oxidations by methyl(trifluoromethyl)dioxirane. 3. Selective polyoxyfunctionalization of adamantane

Adamantane (1) can be converted directly into adamantan-1,3,5-triol (5) and into adamantan-1,3,5,7-tetraol (6) under remarkably mild conditions by employing an excess of isolated methyl(trifluoromethyl)dioxirane (3a) in solution. This new dioxirane species was found to be over 7,000-fold more reactive than dimethyldioxirane (3b) in performing adamantane hydroxylations