Premium
Radical chlorinations of triglycerides
Author(s) -
Sonnet Philip E.,
Osman Stanley
Publication year - 1995
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02541098
Subject(s) - intramolecular force , chemistry , triglyceride , halogenation , carboxylate , fatty acid , surface modification , organic chemistry , medicinal chemistry , cholesterol , biochemistry
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 the bis trifluoroacetate of methyl 9,10‐dihydroxystearate. No products of chlorination on carbons 2–8 were observed.