Allylic-halogenated Oils. I. Allylic Bromination of the Methyl Ester of Mixed Unsaturated Fatty Acids.

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

“…When a three to four-fold excess of NBS was employed, some formation of trienes was observed, but attempts at separation were unsuccessful. Similar studies, including chemical dehydrobromination of allylic brominated unsaturated fatty acid esters also have been reported (108,164,165).…”

Reactions of the Hydrocarbon Chain of Fatty Acids.

“…The relative proportions of these products have not been established. Other reports of allylic halogenation, using A-bromosuccinimide (216,355,383,477,521,543) or ieri-butyl hypochlorite (52,544,549) with various unsaturated fatty acids or mixtures thereof, have not included definite characterization of the products. This work has been directed largely toward increasing the unsaturation of the fatty acid molecule through halogenation followed by dehydrohalogenation (see pages 132 and 133).…”

“…Other work on the dehydrobromination of the products of the allylic bromination of unsaturated fatty acids or esters has utilized a variety of organic and inorganic bases. These include Co203 (366), pyridine, potassium carbonate, ammonia, sodium acetate, am-monium carbonate, calcium oxide, and magnesium oxide (383). Individual products of these reactions were not reported.…”