The Baeyer-Villiger reaction of pinanones (bicyclo[3.1.1]heptanones)

Article abstract of DOI:10.1016/S0040-4020(01)88515-X

The Baeyer-Villiger reaction of bicyclo[3.1.1]heptanones yields the expected lactones, but with some difficulty. These lactones readily react with alcohols, including the ethanol present in commercial chloroform, to give the corresponding hydroxy esters. Pinocamphone and isopinocamphone exhibit conformational control in the Baeyer-Villiger reaction, the trans-isomer yielding mainly the expected lactone, the cis-isomer (isopinocamphone) yielding hydroxyisopinocamphone. The use of this pathway as a synthetic route to cyclobutane monoterpenoids is discussed.