Download PDF
Synthesis 2001; 2001(3): 0451-0457
DOI: 10.1055/s-2001-11433
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >