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 of 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 expoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.