Synthesis of 2,2′-oxirane fatty esters and a study of some of their physical properties

✍ Scribed by Marcel S.F. Lie Ken Jie; Y.F. Zheng

• Publisher: Elsevier Science
• Year: 1988
• Tongue: English
• Weight: 379 KB
• Volume: 46
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(88)90021-7

✦ Synopsis

Two-phase methylene transfer reaction involving methyl 12-oxo-octadecanoate and trimethylsulfonium methysulfate gave methyl 12-(2,2'-oxiran-2-yl)-octadecanoate, while methyl 9,10-and 9,12-dioxooctadecanoate furnished the corresponding methyl 2,2'-bioxiran-2-yl-octadecanoate derivatives. The methylene protons of the 2,2'-oxirane system were characterized by a singlet signal at 2.57d (IH-NMR), and by signals at 52.50 and 59.54 ppm corresponding to the methylene and quaternary carbon atoms, respectively (13C-NMR). Acid-catalysed ring opening reaction facilitated bond rupture between the quaternary carbon and the oxygen of the 2,2'-oxirane system, furnishing the corresponding methoxy-carbinol derivative in the case of methyl 12-(2,2'oxiran-2-yl)-octadecanoate.