Abstract
The NMR spectrum of the crystalline tetrabromide obtained from bromination of linoleic acid exhibited an AA ‘XX’ splitting pattern for the C-11 hydrogens, indicative of a racemic structure rather than a meso for the brominated part of the molecule. Thus, the crystalline isomer is a racemic mixture of 9 R, 10 R, 12 R, 13 R-tetrabromooctadecanoic acid and 9 S, 10 S, 12 S, 13 S-tetrabromooctadecanoic acid. The C-11 methylene spectrum of the liquid tetrabromide was treated as an ABX2 pattern; thus, this isomer is a mixture of 9 R, 10 R, 12 S, 13 S-tetrabromooctadecanoic acid and 9 S, 10 S, 12 R, 13 R-tetrabromo-octadecanoic acid.
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Olson, E.S. The stereochemistry of linoleic acid tetrabromides. J Am Oil Chem Soc 52, 319–321 (1975). https://doi.org/10.1007/BF02637736
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DOI: https://doi.org/10.1007/BF02637736