Sandra Fuermeier et.al.: Expanding the Field of Phosphorus-Containing Fatty Acid Derivatives:Synthesis of 1,2-Oxaphospholene Derivatives and Alkenyl Phosphonates from
a-Keto Allenes

Author(s): Sandra Fuermeier, Maureen M. L. Lau, Marcel S. F. Lie Ken Jie,[, Arne Luetzen, Juergen O. Metzger

Title: Expanding the Field of Phosphorus-Containing Fatty Acid Derivatives:

Date of Upload: 2003

Article: Eur. J. Org. Chem. 2003, 4874-4878, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany, Department of Chemistry, The University of Hong Kong,Pokfulam Road, Hong Kong, SAR, China

Keywords: Alkenes, Allenes, Fatty acids, NMR spectroscopy, Phosphites, sustainable development, renewable feedstock, vegetable oil, plant oil

Abstract:
The first successful preparation of phosphorus-containing heterocyclic fatty acid derivatives is described. Reaction ofthe C18 a-keto allene 1 and the C18 a-keto chloroallene 2 with trimethyl phosphite gave the 1,2-oxaphospholene derivatives 4 and 6, respectively. Hydrolysis of 4 and 6 furnished the corresponding alkenyl phosphonate 5 and alkenyl chlorophosphonate 7, respectively. a-Chloro-a' keto allene 3 gave the oxaphospholene derivative 8. The various intermediates and products were identified by a combination of spectroscopic and spectrometric techniques.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/101.pdf (application/pdf)


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