M. Jie, Y. Zheng
Mar 1, 1988
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Influential Citations
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Journal
Chemistry and Physics of Lipids
Abstract
Abstract 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 (1H-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.