Regio- and Stereoselective Synthesis of Symmetrical and Unsymmetrical 1,3-Diphosphoryl(Phosphonyl, Phosphinyl) Substituted (E)-Propenes

Xiyan Lu; Xiaochun Tao; Jingyang Zhu; Xiaowei Sun; Jingyan Xu

doi:10.1055/s-1989-27407

Synthesis 1989; 1989(11): 848-850
DOI: 10.1055/s-1989-27407

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Regio- and Stereoselective Synthesis of Symmetrical and Unsymmetrical 1,3-Diphosphoryl(Phosphonyl, Phosphinyl) Substituted (E)-Propenes

Xiyan Lu^* , Xiaochun Tao, Jingyang Zhu, Xiaowei Sun, Jingyan Xu

^*Shanghai Institute of Organic Chemisty, Academia Sinica, 345 Lingling Lu, Shanghai 200032, People's Republic of China

Abstract

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Symmetrical and unsymmetrical 1,3-diphosphoryl substituted (E)-propenes were synthesized by the reaction of 1-acetoxyallyl substituted phosphorus compounds (phosphonates, phosphinates, and phosphine oxides) with O,O-dialkyl phosphonates (O-alkyl phosphinates, or dialkyl phosphine oxides) and bis(trimethylsilyl)acetamide (BSA) in the presence of nickel(II) chloride as catalyst, or with trivalent phosphorus acid esters (phosphites, phosphonites, and phosphinites) using only nickel(II) chloride as the catalyst.

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