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Polyunsaturated nitroalkanes and nitro-substituted fatty acids

Easton, Christopher; Xia, Ling; Pitt, Michael; Ferrante, Antonio; Poulos, Alf; Rathjen, Deborah A


Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b with methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols 1a,b gives the corresponding aldehydes 9a,b, which react by Henry condensation with nitromethane to give β-hydroxynitroalkanes 10a,b.

CollectionsANU Research Publications
Date published: 2001
Type: Journal article
Source: Synthesis


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