The rate of ring opening of γ- and δ-lactones derived from meadowfoam fatty acids

delta-Lactones derived from meadowfoam (Limnanthes) fatty acids were reacted with amine and alcohol nucleophiles in a second-order reaction to provide the acyclic 5-hydroxy eicosanoic acid esters and amides. The 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 derivatization of meadowfoam fatty acids. delta-Lactones showed a much larger rate for the formation of derivatives than the corresponding gamma-lactones or fatty acids. delta-Lactone had a rate constant >7700. times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from delta-lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.