G. G. Abbot, F. Gunstone
Dec 1, 1971
Citations
0
Influential Citations
36
Citations
Journal
Chemistry and Physics of Lipids
Abstract
Abstract β-Hydroxy alkenes (such as methyl ricinoleate) furnish 1,2-epoxides by the normal epoxidation process but γ-hydroxy alkenes (such as methyl 9-hydroxyoctadec- cis -12-enoate and methyl threo -12,13-dihydroxyoleate), under the same reaction conditions, give 1,4-epoxides. The epoxidation of β- and γ-oxo alkenes gives mixed products, some of which are not stable. The rearrangement of methyl 9,10-epoxy-12-hydroxystearate (9,12-epoxide) and of methyl 9,10;12,13-diepoxystearate (dioxo and furanoid esters), under the influence of boron trifluoride, gives the products indicated. A 9,12 C 18 furanoid ester is also formed by the reaction of methyl trans -11,12-epoxyoctadec-9-ynoate with aqueous methanolic acidic mercuric sulphate.