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Synthesis 1993; 1993(7): 705-713
DOI: 10.1055/s-1993-25926
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Novel Synthesis of α-Acetylstyrylphosphonates

Ryozo Sakoda* , Hiroo Matsumoto, Kiyotomo Seto
  • *Central Research Institute, Nissan Chemical IND., LTD., Tsuboi 722-1, Funabashi, Chiba, 274, Japan
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Publication History

Publication Date:
17 September 2002 (online)

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α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (aminals). 4-Benzylidenemorpholinium carboxylates, generated from aminals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.