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The stereochemistry of linoleic acid tetrabromides
Author(s) -
Olson Edwin S.
Publication year - 1975
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/bf02637736
Subject(s) - linoleic acid , chemistry , methylene , stereochemistry , molecule , nuclear magnetic resonance spectroscopy , organic chemistry , fatty acid
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 ABX 2 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.