Synthesis ofGEM-dibromocyclopropanoid fatty esters using phenyl (tribromomethyl) mercury

Thegem-dibromocyclopropanation of naturally occurring unsaturated hydroxy fatty esters, methyl ricinoleate (I) and methyl isoricinoleate (II), has been undertaken to provide compounds which might have potential utility. Phenyl(tribromomethyl)mercury reacts only with the carbon-carbon double bond of each substrate, leaving the OH group intact. The product, methyl 9,10-dibromomethylene-12-hydroxyoctadecanoate (III) and methyl 12,13-dibromomethylene-9-hydroxyoctadecanoate (IV), obtained from I and II, respectively, were characterized by elemental, infrared (IR) and nuclear magnetic resonance (NMR) analyses.