Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 5/16/2002
Publication Date: N/A
Technical Abstract: Fats and oils are of interest as renewable raw materials for use by chemical industries. Functionalization of these materials to derive new oleochemicals with interesting properties could help to further expand the uses of fats and oils by these industries. To this end, the ester moiety of several common fatty esters were functionalized to give long-chain compounds containing the isoxazole heterocyclic ring structure. A one-pot reaction sequence, wherein, the ester groups were reacted with an imine anion, followed by reaction with hydroxylamine, and subsequently dehydrated to give the desired lipid isoxazole heterocycles in moderate to good yields. Because the isoxazole ring contains a weak N-O bond, this ring can serve as a versatile synthetic intermediate. Ring opening reactions of the lipid isoxazoles were examined and fatty compounds containing the beta-aminoenones and 1,3-diketone moieties were obtained in good yields. This chemistry allows access to compounds not easily obtained by other methods that may have potentially interesting chemical and physical properties.