Abstract
δ-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 δ-lactones was compared to the rate of ring opening of γ-lactones and the rate of derivatization of meadowfoam fatty acids. δ-Lactones showed a much larger rate for the formation of derivatives than the corresponding γ-lactones or fatty acids. γ-Lactone had a rate constant >7700 times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from δ-lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.
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Isbell, T.A., Steiner, B.A. The rate of ring opening of γ-and δ-lactones derived from meadowfoam fatty acids. J Amer Oil Chem Soc 75, 63–66 (1998). https://doi.org/10.1007/s11746-998-0011-1
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DOI: https://doi.org/10.1007/s11746-998-0011-1