title: 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.
authors.affiliation: Institute of Nanomaterials and Nanotechnology (iNANOTECH), Moroccan Foundation for Advanced Science, Innovation and Research (MAScIR), Avenue de l'Armée Royale, Madinate Al Irfane, 10100 Rabat, Morocco; Laboratoire d'Hétérochimie Fondamentale et Appliquée, UMR CNRS 5069, Université Paul Sabatier, 118, Route de Narbonne, 31062 Toulouse Cedex, France. Electronic address: n.katir@mascir.com.
authors.forename: Nadia
authors.initials: N
authors.lastname: Katir
authors.forename: Abdelkrim
authors.initials: A
authors.lastname: El Kadib
authors.forename: Annie
authors.initials: A
authors.lastname: Castel
mesh_terms: D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D010758:Phosphorus / Q000737:chemistry*; D010766:Phosphorylation
chemical_list: D004952:Esters; D005227:Fatty Acids; D010758:Phosphorus
keywords: Fatty acid; Hydrophosphorylation; Phosphine; Phosphorylated fatty acid diesters