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Expanding the Field of Phosphorus‐Containing Fatty Acid Derivatives: Synthesis of 1,2‐Oxaphospholene Derivatives and Alkenyl Phosphonates from α‐Keto Allenes
Author(s) -
Fürmeier Sandra,
Lau Maureen M. L.,
Lie Ken Jie Marcel S. F.,
Lützen Arne,
Metzger Jürgen O.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300325
Subject(s) - chemistry , allene , phosphonate , hydrolysis , organic chemistry , phosphorus , derivative (finance) , trimethyl phosphite , medicinal chemistry , catalysis , financial economics , economics
The first successful preparation of phosphorus‐containing heterocyclic fatty acid derivatives is described. Reaction of the C 18 α‐keto allene 1 and the C 18 α‐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. α‐Chloro‐α′‐keto allene 3 gave the oxaphospholene derivative 8 . The various intermediates and products were identified by a combination of spectroscopic and spectrometric techniques. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)