Oxidation of 2-methyl-2-hydroxyadamantane by trifluoroperacetic acid i
n trifluoroacetic acid gives oxaadamantane and exo-2-oxaadamantane-4-o
l in a good yield. Other 2-hydroxyadamantane derivatives do not underg
o this transformation. An oxidative cleavage and subsequent cyclizatio
n mechanism is proposed. Copyright (C) 1996 Elsevier Science Ltd