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Synthesis 2001; 2001(3): 0451-0457
DOI: 10.1055/s-2001-11433
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Polyunsaturated Nitroalkanes and Nitro-Substituted Fatty Acids

Christopher J. Easton* , Ling Xia, Michael J. Pitt, Antonio Ferrante, Alfred Poulos, Deborah A. Rathjen
  • *Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia; Fax + 61(2)61 25 81 14; E-mail: easton@rsc.edu.au
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Publikationsdatum:
31. Dezember 2001 (online)

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

Michael additions - carboxylic acids - lipids - Henry reactions - nitroalkanes