Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. III. The Baeyer-Villiger Oxidation of Some Bicycloalkyl Phenyl Ketones

Abstract

The Baeyer-Villiger oxidation of 3β-benzoylbicyclo [3. 3. 1] nonane (1), 8β-benzoylbicyclo [4. 3. 1] decane (2), and 3β-benzoylbicyclo [3. 2. 1] octane (3) is described. The ratio of the main product bicycloalkyl benzoate to its isomeric product phenyl bicycloalkanecarboxylate was determined to be ca. 10 : 1 by the ¹H-NMR measurement of the crude mixture. The Baeyer-Villiger reaction of cyclohexyl phenyl ketone (11) was also carried out and was found to give a similar result in its isomer ratio of the products. The high selectivity in this oxidation enabled the practicable preparation of bicyclo [3. n. 1] alkan-3-ones via bicyclo [3. n. 1] alk-3β-yl phenyl ketones to be achieved.