Synthesis and 19F NMR study of RF-oleic acid-F13

Abstract A seven-step synthesis of Z -13,13,14,14,15,15,16,16,17,17,18,18,18-tridecafluoro-octadec-9-enoic acid (oleic acid-F 13 ) is reported. The key step is a Wittig reaction to form the C9–C10 double bond with a Z : E isomeric ratio greater than 20:1. The 19 F nuclear magnetic resonance (NMR) spectrum is included and unambiguous assignments have been made with the aid of 19 F – 19 F correlation NMR spectroscopy (COSY spectra).