REACTIONS OF DIOXIRANES WITH SELECTED OLEOCHEMICALS

Reaction of fatty acids with dimethyldioxirane in acetone produces ketoacids in 9-12% yields in which the ketone carbonyl is distributed along the fatty chain. The n-1 position appears to be preferred. Lactones oi hydroxy fatty acids are oxidized by this reagent, but in low yields, to the corresponding ketoacids. Biphasic epoxidations with methylethyldioxirane in 2-butanone were conducted with methyl oleate and methyl ricinoleate to give the corresponding epoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.