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Synthesis 1990; 1990(5): 420-422
DOI: 10.1055/s-1990-26893
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Novel Preparation of Vinylphosphonates, Vinylphosphinates, and Vinylphosphine Oxides via ß-Elimination of Nitrous Acid

Mitsuji Yamashita* , Yoshinori Tamada, Akihito Iida, Tatsuo Oshikawa
  • *Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, Hamamatsu 432, Japan
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Publication History

Publication Date:
17 September 2002 (online)

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Base treatment of 2-dimethoxyphosphinyl-, 2-methoxyphenylphosphinyl- and 2-diphenylphosphinyl-1-nitroethane derivatives results in ß-elimination of nitrous acid to afford the corresponding vinyl derivatives in excellent yield. This is a useful method for the preparation of 5,6-dideoxy-5-C-(dimethoxyphosphinyl)-, 5,6-dideoxy-5-C-(methoxyphenylphosphinyl)-, and 5, 6-dideoxy-5-C-(diphenylphosphinyl)-xylo-hexo-5-enofuranose derivatives as well as 5,6-dideoxy-5-C-(dimethoxyphosphinyl)-xylo-hexofuranose.

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