Phosphorus-based fatty acid methyl esters

Abstract

With the aim of designing novel transformable fatty acid diesters, various strategies for introducing phosphorus arms to the fatty backbone have been examined. While lithiated phosphine reacts classically to brominated fatty esters to afford the mono-addition product, the synthesis of phosphorylated diesters was found to be difficult, a fact related to the bulkiness of fatty acids and phosphine reagents. A base-induced dehydrochlorination reaction using ArPCl2 and hydroxy-terminated fatty esters resulted in metastable diester for which hydrolytic cleavage undergo phosphine oxidation and expulsion of one fatty chain. Alternatively, ArPOCl2 alleviates this drawback and provides stable, phosphorylated fatty acid diesters.