THE RATE OF RING-OPENING OF GAMMA-LACTONES AND DELTA-LACTONES DERIVEDFROM MEADOWFOAM FATTY-ACIDS

delta-Lactones derived from meadowfoam (Limnanthes) fatty acids were r eacted with amine and alcohol nucleophiles in a second-order reaction to provide the acyclic 5-hydroxy eicosanoic acid esters and amides. Th e rate of reaction for the ring opening of F-lactones was compared to the rate of ring opening of gamma-lactones and the rate of derivatizat ion of meadowfoam fatty acids. delta-Lactones showed a much larger rat e for the formation of derivatives than the corresponding gamma-lacton es or fatty acids. delta-Lactone had a rate constant >7700. times larg er for the formation of butyl ester than meadowfoam fatty acids. The f ormation of amides from delta-lactones is even faster than the esterif ication reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.