RADICAL CHLORINATIONS OF TRIGLYCERIDES

Several triglycerides were synthesized with an iodoaroyl group. Intram olecular radical chain transfer chlorinations were conducted that resu lted in the associated pair of fatty acids of the triglyceride becomin g chlorinated. The distribution of monochlorinated species was similar to that obtained by direct radical chlorination of the relevant fatty acid methyl esters. Functionalization was, as expected, away from the carboxylate group but gave no indication that either alignment of cha ins or the constraints of an intramolecular process could limit the ma nifold of products of the reaction. To gauge the effect on halogenatio n of a structure, bearing more than one electron-withdrawing group, me thyl oleate was converted to the bis trifluoroacetate of methyl 9,10-d ihydroxystearate. No products of chlorination on carbons 2-8 were obse rved.