Abstract
Several triglycerides were synthesized with an iodoaroyl group. Intramolecular radical chain transfer chlorinations were conducted that resulted in the associated pair of fatty acids of the triglyceride becoming 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 chains or the constraints of an intramolecular process could limit the manifold of products of the reaction. To gauge the effect on halogenation of a structure, bearing more than one electron-withdrawing group, methyl oleate was converted to thebis trifluoroacetate of methyl 9,10-dihydroxystearate. No products of chlorination on carbons 2–8 were observed.
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Sonnet, P.E., Osman, S. Radical chlorinations of triglycerides. J Am Oil Chem Soc 72, 369–374 (1995). https://doi.org/10.1007/BF02541098
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DOI: https://doi.org/10.1007/BF02541098