The ozonolysis of a hydroxymethylene ketone yields a mixture of diketone and anhydride. Treatment of hydroxymethylene camphor with ozone affords, in addition to the expected camphor quinone, a surprisingly large amount of camphoric anhydride (56%) via Baeyer-Villager reaction. Use of infrared absorption to analyze the relative amounts of camphor quinone and camphoric anhydride in a reaction mixture was studied by comparing peak heights of their carbonyl stretching bands.
Yang, Dominic T.C.; Watson, F. H. Jr.; Lay, J. O.; and Getty, R.
"Semiquantitative Infrared Analysis of Diketones and Anhydrides in a Reaction Mixture,"
Journal of the Arkansas Academy of Science: Vol. 30
, Article 39.
Available at: http://scholarworks.uark.edu/jaas/vol30/iss1/39