Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones

Wei Ming Xu; E. Tang; Xian Huang

doi:10.1055/s-2004-829199

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Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones

Wei Ming Xu^a, E Tang^a, Xian Huang*^a,b
^a Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, 310028, P. R. China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;
^b Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China

Abstract

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Abstract

Polystyrene-supported selenomethyl-phosphonate and polystyrene-supported selenomethyl-sulfonates have been prepared. These novel reagents were treated with LDA (or n-BuLi) to produce polystyrene-supported α-seleno carbanions, which reacted with alkyl halides, followed by stereospecific selenoxide syn-elimination to give E-vinylphosphonates and E-vinylsulfones respectively. And also these novel polymer reagents can be regenerated and reused.

Keywords

polystyrene-supported - E-vinylphosphonates - E-vinylsulfones - selenoxide syn-elimination

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