Expanding the Field of Phosphorus‐Containing Fatty Acid Derivatives: Synthesis of 1,2‐Oxaphospholene Derivatives and Alkenyl Phosphonates from α‐Keto Allenes | Zendy

Fürmeier Sandra | Zendy; Lau Maureen M. L. | Zendy; Lie Ken Jie Marcel S. F. | Zendy; Lützen Arne | Zendy; Metzger Jürgen O. | Zendy

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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)

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