Synthesis of sulfur-Containing derivatives from olefinic fatty esters

The reaction of 3-mercaptopropan-l,2-diol with methyl 10-undecenoate (Ib) yielded three products, methyl 11-(3′-mercaptopropan-l′,2′-diacetoxy) undecanoate (II, 48.9%), methyl 11-(1-oxapropan-2′-acetoxy-3′-mercaptoacetyl) undecanoate (III, 27.4%) and methyl 10-(3′-mercaptopropan-1′-acetoxy-2′-ol) undecanoate (IV, 23.0%) along with hydrolyzed starting material (Ia, 5.4%). The same reaction with methyl 9-octadecenoate (Vb) gave an isomeric product, 9(10)-(3′-mercaptopropan-l′-acetoxy-2′-ol) octadecanoic acid (VI, 78.5%) and oleic acid (Va, 21.4%). Reaction withtrans-2-octadecenoic acid (VII) afforded 2(3)-(3′-mercaptopropan-l′-acetoxy-2′-ol) octadecanoic acid (VIII, 85.7%).